Search for "reversible addition fragmentation chain transfer (RAFT)" in Full Text gives 19 result(s) in Beilstein Journal of Organic Chemistry.
Beilstein J. Org. Chem. 2025, 21, 2103–2172, doi:10.3762/bjoc.21.165
Graphical Abstract
Figure 1: C2–C6 biobased carbonyl building blocks.
Scheme 1: Proposed (2 + 2) route to glycolaldehyde and glycolic acid from erythritol by Cu/AC catalyst (AC = ...
Scheme 2: Reductive amination of GCA.
Scheme 3: N-Formylation of secondary amines by reaction with GCA.
Scheme 4: Synthesis and conversion of hydroxy acetals to cyclic acetals.
Scheme 5: Synthesis of 3-(indol-3-yl)-2,3-dihydrofurans via three-component reaction of glycolaldehyde, indol...
Scheme 6: BiCl3-catalyzed synthesis of benzo[a]carbazoles from 2-arylindoles and α-bromoacetaldehyde ethylene...
Scheme 7: Cu/NCNSs-based conversion of glycerol to glycolic acid and other short biobased acids.
Scheme 8: E. coli-based biotransformation of C1 source molecules (CH4, CO2 and CO) towards C2 glycolic acid.
Scheme 9: N-Formylation of amines with C2 (a) or C3 (b) biomass-based feedstocks.
Scheme 10: Methods for the formation of propanoic acid (PA) from lactic acid (LA).
Scheme 11: Co-polymerization of biobased lactic acid and glycolic acid via a bicatalytic process.
Scheme 12: Oxidation of α-hydroxy acids by tetrachloroaurate(III) in acetic acid–sodium acetate buffer medium.
Figure 2: Selective catalytic pathways for the conversion of lactic acid (LA).
Scheme 13: Synthesis of 1,3-PDO via cross-aldol reaction between formaldehyde and acetaldehyde to 3-hydroxypro...
Scheme 14: Hydrothermal conversion of 1,3-dihydroxy-2-propane and 2,3-dihydroxypropanal to methylglyoxal.
Scheme 15: FLS-catalyzed formose reaction to synthesize GA and DHA.
Scheme 16: GCA and DHA oxidation products of glycerol and isomerization of GCA to DHA under flow conditions us...
Scheme 17: Acid-catalyzed reactions of DHA with alcohols.
Scheme 18: Synthesis of dihydroxyacetone phosphate from dihydroxyacetone.
Scheme 19: Bifunctional acid–base catalyst DHA conversion into lactic acid via pyruvaldehyde or fructose forma...
Scheme 20: Catalytic one-pot synthesis of GA and co-synthesis of formamides and formates from DHA.
Scheme 21: (a) Synthesis of furan derivatives and (b) synthesis of thiophene derivative by cascade [3 + 2] ann...
Scheme 22: Brønsted acidic ionic liquid catalyzed synthesis of benzo[a]carbazole from renewable acetol and 2-p...
Scheme 23: Asymmetric hydrogenation of α-hydroxy ketones to 1,2-diols.
Scheme 24: Synthesis of novel 6-(substituted benzylidene)-2-methylthiazolo [2,3-b]oxazol-5(6H)-one from 1-hydr...
Scheme 25: ʟ-Proline-catalyzed synthesis of anti-diols from hydroxyacetone and aldehydes.
Scheme 26: C–C-bond-formation reactions of a biomass-based feedstock aromatic aldehyde (C5) and hydroxyacetone...
Scheme 27: Ethanol upgrading to C4 bulk chemicals via the thiamine (VB1)-catalyzed acetoin condensation.
Scheme 28: One-pot sequential chemoenzymatic synthesis of 2-aminobutane-1,4-diol and 1,2,4-butanetriol via 1,4...
Scheme 29: Synthesis of 1,4-dihydroxybutan-2-one by microbial transformation.
Scheme 30: Conversion of polyols by [neocuproine)Pd(OAc)]2(OTf)2] to α-hydroxy ketones.
Scheme 31: Chemoselective oxidation of alcohols with chiral palladium-based catalyst 2.
Scheme 32: Electrochemical transformation of furfural to 5-hydroxy-2(5H)-furanone (HFO).
Scheme 33: Selective hydrodeoxygenation of HFO and oxidation to γ-butyrolactone (GBL).
Scheme 34: Photosensitized oxygenation of furan towards HFO via ozonide intermediates.
Scheme 35: Conversion of furfural to HFO and MAN by using mesoporous carbon nitride (SGCN) as photocatalyst.
Scheme 36: Synthesis of HFO from furan derivatives.
Scheme 37: Photooxidation of furfural to 5-hydroxy-2(5H)-furanone (HFO).
Scheme 38: Synthesis of Friedel–Crafts indole adduct from HFO.
Scheme 39: Conversion of HFO to α,γ-substituted chiral γ-lactones.
Scheme 40: Tautomeric transformation of HFO to formylacrylic acid.
Scheme 41: Hydrolysis of HFO to succinic acid in aqueous solution.
Scheme 42: Substitution and condensation reactions of 5-hydroxy-2(5H)-furanone (HFO).
Scheme 43: (a) Conversion of HFO towards valuable C4 chemicals and (b) anodic oxidation of 5-hydroxy-2(5H)-fur...
Figure 3: Conversion of HFO towards other natural and synthetic substances.
Scheme 44: Conversion of furfural to maleic anhydride (reaction a: VOx/Al2O3; reaction b: VPO).
Scheme 45: Conversion of furfural into succinic acid.
Scheme 46: Electro‑, photo‑, and biocatalysis for one-pot selective conversions of furfural into C4 chemicals.
Scheme 47: Production route of furfural from hemicellulose.
Scheme 48: Mechanism for xylose dehydration to furfural through a choline xyloside intermediate.
Scheme 49: Conversion of furfural to furfuryl alcohol and its derivatives.
Scheme 50: Conversion of furfural to furfuryl alcohol and 3-(2-furyl)acrolein.
Scheme 51: The aerobic oxidative condensation of biomass-derived furfural and linear alcohols.
Scheme 52: The single-step synthesis of 2-pentanone from furfural.
Scheme 53: Electrocatalytic coupling reaction of furfural and levulinic acid.
Scheme 54: Conversion of furfural to m-xylylenediamine.
Scheme 55: Conversion of furfural to tetrahydrofuran-derived amines.
Scheme 56: Formation of trans-4,5-diamino-cyclopent-2-enones from furfural.
Scheme 57: Production of pyrrole and proline from furfural.
Scheme 58: Synthesis of 1‑(trifluoromethyl)-8-oxabicyclo[3.2.1]oct-3-en-2-ones from furfural.
Scheme 59: Conversion of furfural to furfural-derived diacids.
Scheme 60: A telescope protocol derived from furfural and glycerol.
Scheme 61: A tandem cyclization of furfural and 5,5-dimethyl-1,3-cyclohexanedione.
Scheme 62: A Ugi four-component reaction to construct furfural-based polyamides.
Scheme 63: One-pot synthesis of γ-acyloxy-Cy7 from furfural.
Scheme 64: Dimerization–Piancatelli sequence toward humins precursors from furfural.
Scheme 65: Conversion of furfural to CPN.
Scheme 66: Synthesis of jet fuels range cycloalkanes from CPN and lignin-derived vanillin.
Scheme 67: Solar-energy-driven synthesis of high-density biofuels from CPN.
Scheme 68: Reductive amination of CPN to cyclopentylamine.
Scheme 69: Asymmetric hydrogenation of C=O bonds of exocyclic α,β-unsaturated cyclopentanones.
Scheme 70: Preparation of levulinic acid via the C5 route (route a) or C6 route (routes b1 and b2).
Scheme 71: Mechanism of the rehydration of HMF to levulinic acid and formic acid.
Scheme 72: Important levulinic acid-derived chemicals.
Scheme 73: Direct conversion of levulinic acid to pentanoic acid.
Scheme 74: Catalytic aerobic oxidation of levulinic acid to citramalic acid.
Scheme 75: Conversion of levulinic acid to 1,4-pentanediol (a) see ref. [236]; b) see ref. [237]; c) see ref. [238]; d) see r...
Scheme 76: Selective production of 2-butanol through hydrogenolysis of levulinic acid.
Scheme 77: General reaction pathways proposed for the formation of 5MPs from levulinic acid.
Scheme 78: Selective reductive amination of levulinic acid to N-substituted pyrroles.
Scheme 79: Reductive amination of levulinic acid to chiral pyrrolidinone.
Scheme 80: Reductive amination of levulinic acid to non-natural chiral γ-amino acid.
Scheme 81: Nitrogen-containing chemicals derived from levulinic acid.
Scheme 82: Preparation of GVL from levulinic acid by dehydration and hydrogenation.
Scheme 83: Ruthenium-catalyzed levulinic acid to chiral γ-valerolactone.
Scheme 84: Catalytic asymmetric hydrogenation of levulinic acid to chiral GVL.
Scheme 85: Three steps synthesis of ε-caprolactam from GVL.
Scheme 86: Multistep synthesis of nylon 6,6 from GVL.
Scheme 87: Preparation of MeGVL by α-alkylation of GVL.
Scheme 88: Ring-opening polymerization of five-membered lactones.
Scheme 89: Synthesis of GVL-based ionic liquids.
Scheme 90: Preparation of butene isomers from GVL under Lewis acid conditions.
Scheme 91: Construction of C5–C12 fuels from GVL over nano-HZSM-5 catalysts.
Scheme 92: Preparation of alkyl valerate from GVL via ring opening/reduction/esterification sequence.
Scheme 93: Construction of 4-acyloxypentanoic acids from GVL.
Scheme 94: Synthesis of 1,4-pentanediol (PDO) from GVL.
Scheme 95: Construction of novel cyclic hemiketal platforms via self-Claisen condensation of GVL.
Scheme 96: Copper-catalyzed lactamization of GVL.
Figure 4: Main scaffolds obtained from HMF.
Scheme 97: Biginelli reactions towards HMF-containing dihydropyrimidinones.
Scheme 98: Hantzsch dihydropyridine synthesis involving HMF.
Scheme 99: The Kabachnik–Fields reaction involving HMF.
Scheme 100: Construction of oxazolidinone from HMF.
Scheme 101: Construction of rhodamine-furan hybrids from HMF.
Scheme 102: A Groebke–Blackburn–Bienaymé reaction involving HMF.
Scheme 103: HMF-containing benzodiazepines by [4 + 2 + 1] cycloadditions.
Scheme 104: Synthesis of fluorinated analogues of α-aryl ketones.
Scheme 105: Synthesis of HMF derived disubstituted γ-butyrolactone.
Scheme 106: Functionalized aromatics from furfural and HMF.
Scheme 107: Diels–Alder adducts from HMF or furfural with N-methylmaleimide.
Scheme 108: Pathway of the one-pot conversion of HMF into phthalic anhydride.
Scheme 109: Photocatalyzed preparation of humins (L-H) from HMF mixed with spoiled HMF residues (LMW-H) and fur...
Scheme 110: Asymmetric dipolar cycloadditions on HMF.
Scheme 111: Dipolar cycloadditions of HMF based nitrones to 3,4- and 3,5-substituted isoxazolidines.
Scheme 112: Production of δ-lactone-fused cyclopenten-2-ones from HMF.
Scheme 113: Aza-Piancatelli access to aza-spirocycles from HMF-derived intermediates.
Scheme 114: Cross-condensation of furfural, acetone and HMF into C13, C14 and C15 products.
Scheme 115: Base-catalyzed aldol condensation/dehydration sequences from HMF.
Scheme 116: Condensation of HMF and active methylene nitrile.
Scheme 117: MBH reactions involving HMF.
Scheme 118: Synthesis of HMF-derived ionic liquids.
Scheme 119: Reductive amination/enzymatic acylation sequence towards HMF-based surfactants.
Scheme 120: The formation of 5-chloromethylfurfural (CMF).
Scheme 121: Conversion of CMF to HMF, levulinic acid, and alkyl levulinates.
Scheme 122: Conversion of CMF to CMFCC and FDCC.
Scheme 123: Conversion of CMF to BHMF.
Scheme 124: Conversion of CMF to DMF.
Scheme 125: CMF chlorine atom substitutions toward HMF ethers and esters.
Scheme 126: Introduction of carbon nucleophiles in CMF.
Scheme 127: NHC-catalyzed remote enantioselective Mannich-type reactions of CMF.
Scheme 128: Conversion of CMF to promising biomass-derived dyes.
Scheme 129: Radical transformation of CMF with styrenes.
Scheme 130: Synthesis of natural herbicide δ-aminolevulinic acid from CMF.
Scheme 131: Four step synthesis of the drug ranitidine from CMF.
Scheme 132: Pd/CO2 cooperative catalysis for the production of HHD and HXD.
Scheme 133: Different ruthenium (Ru) catalysts for the ring-opening of 5-HMF to HHD.
Scheme 134: Proposed pathways for preparing HXD from HMF.
Scheme 135: MCP formation and uses.
Scheme 136: Cu(I)-catalyzed highly selective oxidation of HHD to 2,5-dioxohexanal.
Scheme 137: Synthesis of N‑substituted 3‑hydroxypyridinium salts from 2,5-dioxohexanal.
Scheme 138: Ru catalyzed hydrogenations of HHD to 1,2,5-hexanetriol (a) see ref. [396]; b) see ref. [397]).
Scheme 139: Aviation fuel range quadricyclanes produced by HXD.
Scheme 140: Synthesis of HDGK from HXD and glycerol as a chain extender.
Scheme 141: Synthesis of serinol pyrrole from HXD and serinol.
Scheme 142: Synthesis of pyrroles from HXD and nitroarenes.
Scheme 143: Two-step production of PX from cellulose via HXD.
Scheme 144: Preparation of HCPN from HMF via hydrogenation and ring rearrangement.
Scheme 145: Suggested pathways from HMF to HCPN.
Scheme 146: α-Alkylation of HCPN with ethylene gas.
Scheme 147: Synthesis of 3-(hydroxymethyl)cyclopentylamine from HMF via reductive amination of HCPN.
Scheme 148: Production of LGO and Cyrene® from biomass.
Scheme 149: Synthesis of HBO from LGO and other applications.
Scheme 150: Construction of m-Cyrene® homopolymer.
Scheme 151: Conversion of Cyrene® to THFDM and 1,6-hexanediol.
Scheme 152: RAFT co-polymerization of LGO and butadienes.
Scheme 153: Polycondensation of HO-LGOL and diols with dimethyl adipate.
Scheme 154: Self-condensation of Cyrene® and Claisen–Schmidt reactions.
Scheme 155: Synthesis of 5-amino-2-(hydroxymethyl)tetrahydropyran from Cyrene®.
Beilstein J. Org. Chem. 2025, 21, 935–944, doi:10.3762/bjoc.21.76
Graphical Abstract
Figure 1: D–A–D organic PCs previously reported and our new D–A bimodal organic PCs.
Figure 2: Selected frontier MOs and relative calculated energies of D–A photocatalysts (4a,5a–e, and 6a). Abs...
Figure 3: Comparison of the ground state redox potential of the acceptor moieties (4–6), the donor moieties (a...
Beilstein J. Org. Chem. 2024, 20, 2129–2142, doi:10.3762/bjoc.20.183
Graphical Abstract
Scheme 1: Esterification of oleic acid (1) with propylsulfonic acid (Pr-SO3H)-functionalised mesoporous silic...
Scheme 2: Using confinement of organocatalytic units for improving the enantioselectivity of silica-supported...
Scheme 3: Michael addition catalysed by cinchona thiourea immobilised on magnetic nanoparticles (13).
Scheme 4: Michael addition catalysed by cinchona thiourea in the presence of magnetic nanoparticles.
Scheme 5: Benzoin condensation catalysed by N-benzylthiazolium salt attached to mesoporous material.
Scheme 6: Photoinduced RAFT polymerisation of n-butyl acrylate (19) catalysed by silica nanoparticle-supporte...
Scheme 7: Pressure and temperature dependence of the 1,4-addition of propanal to trans-β-nitrostyrene under c...
Scheme 8: α-Amination of ethyl 2-oxocyclopentanecarboxylate catalysed by PS-THU which could be recycled over ...
Scheme 9: Preparation of supported catalysts C29–C31 from cinchona squaramides 29–31 modified with a primary ...
Scheme 10: Application of PGMA-supported organocatalysts C29–C31 in the asymmetric Michael addition of pentane...
Scheme 11: Alcoholytic desymmetrisation of a cyclic anhydride 34 catalysed by polyamide-supported cinchona sul...
Beilstein J. Org. Chem. 2023, 19, 1580–1603, doi:10.3762/bjoc.19.116
Graphical Abstract
Scheme 1: Oxidation of catechol and subsequent cross-linking. Scheme 1 redrawn from [3].
Scheme 2: (A) Structure of typical urushiol in Chinese lacquer, and (B) schematic process of laccase-catalyze...
Scheme 3: A) Primary amino acid sequence of mfp-1, mfp-3, and mfp-5 (Y: DOPA, K: lysine). B) Scheme showing e...
Scheme 4: Activation–deactivation equilibrium in nitroxide-mediated polymerizations. Bicomponent initiating s...
Scheme 5: Mechanism of a transition metal complex-mediated ATRP. Scheme 5 redrawn from [14].
Scheme 6: Mechanism of RAFT polymerization. Scheme 6 redrawn from [68].
Scheme 7: Degenerative transfer (a) and reversible termination (b) mechanism of OMRP. Scheme 7 redrawn from [70].
Scheme 8: Simplified mechanism of a RITP. Scheme 8 redrawn from [21].
Scheme 9: (A) Structures of π-conjugated conductive polymers. (B) Examples of conductive polymer synthesis vi...
Scheme 10: Possible regiochemical couplings in PATs. Scheme 10 redrawn from [79].
Scheme 11: General thiol-ene photopolymerization process. Scheme 11 redrawn from [81].
Scheme 12: (a) Three generations of Grubbs catalysts. (b) Proposed mechanism for photo-ROMP via a reductive qu...
Scheme 13: Pyrylium and thiopyrylium salts studied by Boydston et al. Scheme 13 redrawn from [91].
Scheme 14: A general illustration of post-polymerization modification by thiol–ene chemistry.
Scheme 15: Introduction of functionalities by nitroxide radical coupling of HO-TEMPO derivatives.
Scheme 16: Chemical reaction process scheme of DCP-induced crosslinking of LDPE. Scheme 16 redrawn from [126].
Scheme 17: A probable mechanism of radical-induced hydrosilylation.
Scheme 18: Polymer surface modification by homolytic dediazonation of diazonium salts.
Scheme 19: Photoinduced polymer surface modification or surface grafting using benzophenone.
Scheme 20: Depolymerization mechanism of common photoresists. (a) A possible mechanism of radiation decomposit...
Scheme 21: Proposed mechanisms of photooxidative depolymerization of polystyrene. (a) Scheme 21a was reprinted with perm...
Beilstein J. Org. Chem. 2021, 17, 139–155, doi:10.3762/bjoc.17.15
Graphical Abstract
Figure 1: Chemical structures of representative macrocycles.
Figure 2: Ba2+-induced intermolecular [2 + 2]-photocycloaddition of crown ether-functionalized substrates 1 a...
Figure 3: Energy transfer system constructed of a BODIPY–zinc porphyrin–crown ether triad assembly bound to a...
Figure 4: The sensitizer 5 was prepared by a flavin–zinc(II)–cyclen complex for the photooxidation of benzyl ...
Figure 5: Enantiodifferentiating Z–E photoisomerization of cyclooctene sensitized by a chiral sensitizer as t...
Figure 6: Structures of the modified CDs as chiral sensitizing hosts. Adapted with permission from [24], Copyrigh...
Figure 7: Supramolecular 1:1 and 2:2 complexations of AC with the cationic β-CD derivatives 16–21 and subsequ...
Figure 8: Construction of the TiO2–AuNCs@β-CD photocatalyst. Republished with permission of The Royal Society...
Figure 9: Visible-light-driven conversion of benzyl alcohol to H2 and a vicinal diol or to H2 and benzaldehyd...
Figure 10: (a) Structures of CDs, (b) CoPyS, and (c) EY. Republished with permission of The Royal Society of C...
Figure 11: Conversion of CO2 to CO by ReP/HO-TPA–TiO2. Republished with permission of The Royal Society of Che...
Figure 12: Thiacalix[4]arene-protected TiO2 clusters for H2 evolution. Reprinted with permission from [37], Copyri...
Figure 13: 4-Methoxycalix[7]arene film-based TiO2 photocatalytic system. Reprinted from [38], Materials Today Chem...
Figure 14: (a) Photodimerization of 6-methylcoumarin (22). (b) Catalytic cycle for the photodimerization of 22...
Figure 15: Formation of a supramolecular PDI–CB[7] complex and structures of monomers and the chain transfer a...
Figure 16: Ternary self-assembled system for photocatalytic H2 evolution (a) and structure of 27 (b). Figure 16 reprodu...
Figure 17: Structures of COP-1, CMP-1, and their substrate S-1 and S-2.
Figure 18: Supramolecular self-assembly of the light-harvesting system formed by WP5, β-CAR, and Chl-b. Reprod...
Figure 19: Photocyclodimerization of AC based on WP5 and WP6.
Beilstein J. Org. Chem. 2020, 16, 415–444, doi:10.3762/bjoc.16.40
Graphical Abstract
Scheme 1: Structural patterns of several symmetric cyanines relating to trimethines (I), pentamethines (II), ...
Scheme 2: 1-Substituted 2,3,3-trimethylindolium-, 2,3,3-benzo[e]indolium-, and 2,3,3-benzo[c,d]indolium salts...
Scheme 3: Substitution of the chlorine substituent at the meso-position by a stronger nucleophilic moiety B [68].
Scheme 4: Structure of alternative chain builders for synthesis of heptamethines.
Figure 1: Simplified process chart of photophysical processes occurring in NIR absorbers.
Scheme 5: Chemical structure of the electron acceptors that were from iodonium cations 88 and triazines 89.
Figure 2: Photoinduced electron transfer under different scenarios in which each example exhibits an intrinsi...
Scheme 6: Photoexcited absorber 33 results in reaction with an iodonium cation in the respective cation radic...
Scheme 7: Reaction scheme of absorbers comprising in the molecules center a five ring bridged moiety. This le...
Scheme 8: Structure of donor compounds used in a three component system.
Figure 3: Cationic photopolymerization of an epoxide (Epikote 828) initiated by excitation of the absorber 36...
Scheme 9: Different modes of photoinitiated ATRP using UV, visible and NIR light.
Scheme 10: The structure of Sens used in photo-ATRP.
Figure 4: Comparison of the GPC traces of precursor PMMA with a) chain extended PMMA and b) PMMA-b-PS. Condit...
Figure 5: Spectral changes of the solution of 48 in the presence of [Cu(L)]Br2 (L: tris(2-pyridylmethyl)amine...
Scheme 11: Photoinduced CuAAC reactions in which photochemical reactions result in formation of the Cu(I) cata...
Scheme 12: Model reaction between benzyl azide and phenyacetylene using the absorber 48 as NIR sensitizer at 7...
Figure 6: Block copolymerization of the precursors PS-N3 and Alkyne-PCL results in the block copolymer PS-b-P...
Figure 7: UV–vis–NIR absorption changes of the solution of 48 in the presence of PMDETA, phenylacetylene and ...
Scheme 13: Workflow to design and process new materials in a setup based on an intelligent DoE to develop tech...
Scheme 14: Illustration of the iDoE setting up experiments suggested and analyzed by the A.I. After defining t...
Scheme 15: Classification of the factors for the formation of polymer networks by NIR-photocuring depending on...
Beilstein J. Org. Chem. 2018, 14, 3047–3058, doi:10.3762/bjoc.14.283
Graphical Abstract
Scheme 1: Degenerative radical transfer of xanthates to olefins.
Scheme 2: Photocatalytic RAFT polymerization of xanthate 4.
Figure 1: Photoluminescence (PL) spectra of the 3MLCT state of 8 in degassed DMSO solvent with (A) various co...
Figure 2: (A) ns-Transient absorption spectra of photocatalyst 8 in degassed DMSO recorded at different delay...
Figure 3: UV–vis absorption spectrum of 1a (1 mM solution in DMSO).
Scheme 3: Determination of quantum yield.
Scheme 4: Proposed reaction mechanism.
Beilstein J. Org. Chem. 2017, 13, 2186–2213, doi:10.3762/bjoc.13.219
Graphical Abstract
Figure 1: Summary of the synthetic routes to prepare phosphonic acids detailed in this review. The numbers in...
Figure 2: Chemical structure of dialkyl phosphonate, phosphonic acid and illustration of the simplest phospho...
Figure 3: Illustration of some phosphonic acid exhibiting bioactive properties. A) Phosphonic acids for biome...
Figure 4: Illustration of the use of phosphonic acids for their coordination properties and their ability to ...
Figure 5: Hydrolysis of dialkyl phosphonate to phosphonic acid under acidic conditions.
Figure 6: Examples of phosphonic acids prepared by hydrolysis of dialkylphosphonate with HCl 35% at reflux (16...
Figure 7: A) and B) Observation of P–C bond breaking during the hydrolysis of phosphonate with concentrated H...
Figure 8: Mechanism of the hydrolysis of dialkyl phosphonate with HCl in water.
Figure 9: Hydrolysis of bis-tert-butyl phosphonate 28 into phosphonic acid 29 [137].
Figure 10: A) Hydrolysis of diphenyl phosphonate into phosphonic acid in acidic media. B) Examples of phosphon...
Figure 11: Suggested mechanism occurring for the first step of the hydrolysis of diphenyl phosphonate into pho...
Figure 12: A) Hydrogenolysis of dibenzyl phosphonate to phosphonic acid. B) Compounds 33, 34 and 35 were prepa...
Figure 13: A) Preparation of phosphonic acid from diphenyl phosphonate with the Adam’s catalyst. B) Compounds ...
Figure 14: Suggested mechanism for the preparation of phosphonic acid from dialkyl phosphonate using bromotrim...
Figure 15: A) Reaction of the phosphonate-thiophosphonate 37 with iodotrimethylsilane followed by methanolysis...
Figure 16: Synthesis of hydroxymethylenebisphosphonic acid by reaction of tris(trimethylsilyl) phosphite with ...
Figure 17: Synthesis of the phosphonic acid disodium salt 48 by reaction of mono-hydrolysed phosphonate 47 wit...
Figure 18: Phosphonic acid synthesized by the sequence 1) bromotrimethylsilane 2) methanolysis or hydrolysis. ...
Figure 19: Polyphosphonic acids and macromolecular compounds prepared by the hydrolysis of dialkyl phosphonate...
Figure 20: Examples of organometallic complexes functionalized with phosphonic acids that were prepared by the...
Figure 21: Side reaction observed during the hydrolysis of methacrylate monomer functionalized with phosphonic...
Figure 22: Influence of the reaction time during the hydrolysis of compound 76.
Figure 23: Dealkylation of dialkyl phosphonates with boron tribromide.
Figure 24: Dealkylation of diethylphosphonate 81 with TMS-OTf.
Figure 25: Synthesis of substituted phenylphosphonic acid 85 from the phenyldichlorophosphine 83.
Figure 26: Hydrolysis of substituted phenyldichlorophosphine oxide 86 under basic conditions.
Figure 27: A) Illustration of the synthesis of chiral phosphonic acids from phosphonodiamides. B) Examples of ...
Figure 28: A) Illustration of the synthesis of the phosphonic acid 98 from phosphonodiamide 97. B) Use of cycl...
Figure 29: Synthesis of tris(phosphonophenyl)phosphine 109.
Figure 30: Moedritzer–Irani reaction starting from A) primary amine or B) secondary amine. C) Examples of phos...
Figure 31: Phosphonic acid-functionalized polymers prepared by Moedritzer–Irani reaction.
Figure 32: Reaction of phosphorous acid with imine in the absence of solvent.
Figure 33: A) Reaction of phosphorous acid with nitrile and examples of aminomethylene bis-phosphonic acids. B...
Figure 34: Reaction of carboxylic acid with phosphorous acid and examples of compounds prepared by this way.
Figure 35: Synthesis of phosphonic acid by oxidation of phosphinic acid (also identified as phosphonous acid).
Figure 36: Selection of reaction conditions to prepare phosphonic acids from phosphinic acids.
Figure 37: Synthesis of phosphonic acid from carboxylic acid and white phosphorus.
Figure 38: Synthesis of benzylphosphonic acid 136 from benzaldehyde and red phosphorus.
Figure 39: Synthesis of graphene phosphonic acid 137 from graphite and red phosphorus.
Beilstein J. Org. Chem. 2017, 13, 1310–1315, doi:10.3762/bjoc.13.127
Graphical Abstract
Scheme 1: Synthesis route of RAMEB based statistical polyrotaxane.
Figure 1: (a) GPC trace of the polyHEMA-co-polyisoprene polyrotaxane 1 and (b) 500 MHz 1H NMR and DOSY spectr...
Scheme 2: Schematic representation of the synthetic procedure for the preparation of randomly methylated β-CD...
Figure 2: (a) GPC traces of the macroCTA 5 (solid line) and the poly(TRIS-AAm)-b-polyisoprene-b-poly(TRIS-AAm...
Beilstein J. Org. Chem. 2017, 13, 1008–1021, doi:10.3762/bjoc.13.100
Graphical Abstract
Figure 1: Schematic overview on the glyco-gold nanoparticles synthetic approaches.
Figure 2: Glyco-gold nanoparticles: metallic core and glyco-coating contribute to the production of the versa...
Figure 3: The protein–carbohydrate interactions analyzed by conventional dark field microscopy. The interacti...
Figure 4: Copper-free cycloaddition (SPAAC) of azido galactoside on cyclooctyne and schematic depiction of Au...
Figure 5: A photoaffinity labeling (PAL) approach based on glyco-gold nanoparticles is able to recognize and ...
Figure 6: Design of the fiber-type “Sugar Chips”. AuNPs are firstly immobilized on an optical fiber functiona...
Figure 7: Design of GAuNPs, displaying both sugar residues and the anticancer Au(I)PPh3. Reprinted with permi...
Beilstein J. Org. Chem. 2017, 13, 65–75, doi:10.3762/bjoc.13.9
Graphical Abstract
Figure 1: Typical pilot scale single screw extruder (left) and a laboratory scale twin screw extruder (right)....
Figure 2: PTFE screw employed in single screw extrusion, with increasing root diameter (RD) from 45 mm to 95 ...
Figure 3: Modulated stainless steel intermeshing co-rotating screws employed typically in twin screw extrusio...
Scheme 1: Polymerisation of styrene using s-BuLi as an initiator.
Scheme 2: Telescoping process of the formation of polystyrene, followed by post polymerisation functionalisat...
Scheme 3: Proposed mechanism for the branching of polylactide. Adapted from [23].
Scheme 4: Chemical reaction between isocyanate and an alcohol to form polyurethane.
Figure 4: Representative diagram explaining the process involved in step growth polymerisation, which involve...
Scheme 5: Generic polycondensation reaction to produce polyamides.
Figure 5: Comparison of choline chloride/D-fructose DES prepared via twin screw extrusion (left) and conventi...
Scheme 6: Synthesis of HKUST-1, ZIF-8 and Al(fumarate)OH by twin screw extrusion. Adapted from [2].
Figure 6: Synthesis of Ni(NCS)2(PPh3)2 and [Ni(salen)] by twin screw extrusion. Adapted from [2].
Beilstein J. Org. Chem. 2016, 12, 2495–2502, doi:10.3762/bjoc.12.244
Graphical Abstract
Figure 1: Preparation scheme of α-CD-CTA.
Figure 2: Crystal structure of α-CD with N,N-dimethylacrylamide (DMA). (a) The structure of an 1:1 inclusion ...
Figure 3: Time-conversion curves (a), kinetic plots (b) and plots of number-average molecular weight (Mn) ver...
Figure 4: Proposed polymerization mechanism for a water-soluble vinyl monomer with α-CD-CTA as a chain transf...
Beilstein J. Org. Chem. 2016, 12, 2378–2389, doi:10.3762/bjoc.12.232
Graphical Abstract
Figure 1: Structures of used monomers and the time-conversion plot of the corresponding free-radical polymeri...
Scheme 1: Stereospecific propagation of chiral MLA illustrating the triade formation [15].
Figure 2: Plot of log Pn versus log [In] of the polymerization of MLA with different mol % AIBN.
Scheme 2: Postulated mechanism of the self-initiation of MLA.
Figure 3: DFT-calculated C–C binding length (yellow) of (A) MLA and (B) the corresponding radical.
Figure 4: IR spectra of (A) MLA and of (B) poly(MLA) prepared by the self-initiated polymerization at 70 °C.
Figure 5: Conversion plot of the polymerization of MLA in 1,4-dioxane and DMF (cMLA = 1.8 mol L−1, cAIBN = 1....
Figure 6: UV–vis spectra of the reaction mixture with DPPH radical at the beginning (violet line, 0.23 mM) of...
Figure 7: Copolymer composition curves for the systems MLA with styrene and MMA.
Figure 8: 1H NMR spectrum of MLA with 1 equiv of thioacetic acid and 0.15 equivalents of an inhibitor 4-metho...
Scheme 3: Mechanism of RAFT polymerization [24].
Figure 9: Structures of used RAFT agents examined in the polymerization of MLA.
Figure 10: A) Kinetic plot for the RAFT copolymerization of MLA and DMA for the ratio 90/10 employing EMP. B) ...
Beilstein J. Org. Chem. 2015, 11, 2747–2762, doi:10.3762/bjoc.11.296
Graphical Abstract
Scheme 1: Synthesis of homopolymers containing ferrocenyl and tetraethylene glycol groups.
Scheme 2: Synthesis of redox-robust triazolylbiferrocenyl polymers 4.
Scheme 3: Synthesis of cobaltocenium-containing polymers by ROMP.
Scheme 4: Cobaltocenium-appending copolymers by the ROMP approach (X = PF6, Y = BPh4 or Cl).
Scheme 5: Cobalt-containing polymers by click and ROMP approach.
Scheme 6: Synthesis of new cobalt-integrating block copolymers.
Scheme 7: Two alternative routes for the synthesis of redox-active cobalticenium-tethered polyelectrolytes.
Scheme 8: Oxanorbornene monomers for the synthesis of Ru-containing polymers by ROMP.
Scheme 9: ROMP synthesis of Ru-containing homopolymers.
Scheme 10: Synthesis of diblock copolymers incorporating ruthenium.
Scheme 11: Synthesis of Ru triblock copolymers.
Scheme 12: Synthesis of cross-linked Ru-containing triblock copolymers.
Scheme 13: Synthesis of Ir-containing homopolymers by ROMP.
Scheme 14: Monomers for Ir- and Os-containing ROMP polymers.
Scheme 15: ROMP block copolymers integrating Ir in their side chains.
Scheme 16: Synthesis of Rh-containing block copolymers.
Scheme 17: Access to rhodocenium-containing metallopolymers by ROMP.
Scheme 18: Synthesis of homopolymers equipped with Cu coordination centers.
Scheme 19: Synthesis of Cu-containing copolymers (spacer = –(CH2)5–; >C=O).
Scheme 20: Synthesis of polynorbornene bearing a polyoxometalate (POM) cluster in the side chain.
Scheme 21: Synthesis of Eu-containing copolymers by a ROMP-based route.
Beilstein J. Org. Chem. 2015, 11, 837–847, doi:10.3762/bjoc.11.93
Graphical Abstract
Figure 1: Comparing the entropy loss during ligand–receptor interactions in dependence of the rigidity of the...
Scheme 1: Selection of three polymer carriers differing with respect to backbone flexibility, and morphology ...
Figure 2: Representative ITC-measurements conducted at 8 °C with the peptide–polymer conjugates A) pHPMA-1 an...
Figure 3: Enthalpic and entropic contributions to the free energy of binding processes of multivalent peptide...
Figure 4: MD simulations over time (0–100 ns) yielding A) the mean sulfur distance between two peptides at th...
Figure 5: MD simulation image showing the interaction of two dextran–peptide conjugates with three tandem WW ...
Beilstein J. Org. Chem. 2015, 11, 446–468, doi:10.3762/bjoc.11.51
Graphical Abstract
Scheme 1: Selective O-acetylation of hydroxyamino acids with acetic anhydride in perchloric acid-acetic acid ...
Scheme 2: Selective O-acetylation of L-tyrosine as reported by Bretschneider and Biemann in 1950 [13].
Scheme 3: Selective O-acetylation of L-serine in acetic acid saturated with hydrogen chloride as reported by ...
Scheme 4: Chemoselective O-acetylation of hydroxyamino acids with acetyl chloride in hydrochloric acid–acetic...
Scheme 5: Chemoselective O-acylation of hydroxyamino acids with acyl chlorides in anhydrous trifluoroacetic a...
Scheme 6: Chemoselective O-acylation of hydroxyproline with acyl chlorides or carboxylic anhydrides in methan...
Scheme 7: Chemoselective O-acetylation of L-DOPA as reported by Fuller, Verlander and Goodman in 1978 [35].
Scheme 8: Chemoselective O-acylation of L-tyrosine as reported by Huang, Kimura, Bawarshi-Nassar and Hussain ...
Scheme 9: Preparation of proline amphiphiles or acrylic proline monomers (for macromolecular synthesis) by ch...
Scheme 10: Preparation of amphiphilic organocatalysts from serine, threonine and cysteine by chemoselective O-...
Scheme 11: Preparation of amphiphilic proline organocatalysts by chemoselective O-acylation with acyl chloride...
Scheme 12: Amphiphilic organocatalysts prepared from hydroxyamino acids and isosteviol by chemoselective O-acy...
Scheme 13: Preparation of acrylic proline precursors for polymeric organocatalysts by chemoselective O-acylati...
Scheme 14: Conversion of trans-4-hydroxy-L-proline to cis-4-hydroxy-D-proline·HCl and subsequent chemoselectiv...
Scheme 15: Some examples of chemoselective O-acylation of amino alcohols under acidic reaction conditions repo...
Scheme 16: An assembly of chiral acrylic building blocks useful in the synthesis of polymer-supported diphenyl...
Scheme 17: The chemoselective pentaacetylation of D-glucamine under acidic reaction conditions [95].
Beilstein J. Org. Chem. 2013, 9, 1589–1600, doi:10.3762/bjoc.9.181
Graphical Abstract
Figure 1: Structure of the SG1, TEMPO and DBN nitroxides and the BlocBuilder MA alkoxyamine.
Figure 2: Key equilibrium between active and dormant species involved in the nitroxide-mediated (NMP) polymer...
Figure 3: Degradation of the SG1 nitroxide versus time in the presence of 0 (empty stars), 1 (filled squares)...
Figure 4: Degradation of the SG1 (triangles) and TEMPO (squares) nitroxides versus time in the presence of 0 ...
Figure 5: Degradation of the SG1 nitroxide versus time in DMA (filled squares), DMF (filled triangles), MeOH ...
Figure 6: Degradation of the SG1 nitroxide versus time in the presence of 0% of lithium salt in DMA (empty sq...
Figure 7: Degradation of the TEMPO nitroxide versus time in DMA in the presence of 0% lithium salt (empty squ...
Figure 8: NMP of styrene initiated by the BlocBuilder MA alkoxyamine at 120 °C in DMA without LiCl salt. (a) ...
Scheme 1: Synthesis of the cellobiose and SG1-based alkoxyamine (cello-SG1). The shown regioisomer exhibits a...
Figure 9: (a) Evolution of the number-average molar mass (Mn: filled symbol, linear fit: dash lines) and poly...
Scheme 2: (Reversible) redox system of nitroxide.
Figure 10: Cyclic voltammograms in DMF of (a) SG1 (10−2 M)/ NaClO4 (10−1 M) and (b) LiCl (10−2 M)/TBAPF6 (10−1...
Figure 11: Cyclic voltammograms of DMF/4.5 wt % LiBr solution heated at 80 °C for 30 min (plain line) and 14 h...
Scheme 3: Hydrolysis of DMA in the presence of LiCl.
Scheme 4: Disproportionation of nitroxide 1 by acid treatment.
Figure 12: Degradation of the nitroxides (SG1 and TEMPO) in the presence of HCl. (a) TEMPO ESR signal in the p...
Beilstein J. Org. Chem. 2013, 9, 1226–1234, doi:10.3762/bjoc.9.139
Graphical Abstract
Scheme 1: RAFT polymerization and silica-supported RAFT polymerization of vinylbenzyl chloride (VBC).
Figure 1: Evolution of number-average molecular weight (Mn) and Mw/Mn values of the poly(VBC) chains obtained...
Figure 2: Conversion and ln([M]0/[M]) versus time for AIBN-initiated, PABTC-mediated polymerization of VBC at...
Figure 3: AIBN-initiated, PABTC-mediated polymerization of VBC with (triangles, DP 4,400) and without (circle...
Figure 4: Evolution of molecular weights of free and grafted poly(VBC) chains with conversion.
Figure 5: Plot of the average diameter and PDI of particles recovered from silica-supported RAFT polymerizati...
Figure 6: TEM micrographs of particles (A) after 2 hours and (B) after 21 hours of VBC polymerization. Scale ...
Beilstein J. Org. Chem. 2010, 6, No. 66, doi:10.3762/bjoc.6.66
Graphical Abstract
Figure 1: Structures of monomers 1–7 and chain transfer agent 8 used in the RAFT polymerizations.
Figure 2: a) Second derivative UV–vis spectra [17-19] observed during a full titration of a stock solution of RAFT c...
Figure 3: Isothermal calorimetric binding curves for selected polymer/protein host–guest pairs. a) Typical bi...
Figure 4: Graphical illustration of the potential binding mode on hemoglobin tetramer (represented as electro...