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Search for "sulfone" in Full Text gives 115 result(s) in Beilstein Journal of Organic Chemistry.

Direct C2–H alkylation of indoles driven by the photochemical activity of halogen-bonded complexes

  • Martina Mamone,
  • Giuseppe Gentile,
  • Jacopo Dosso,
  • Maurizio Prato and
  • Giacomo Filippini

Beilstein J. Org. Chem. 2023, 19, 575–581, doi:10.3762/bjoc.19.42

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  • and Technology Alliance (BRTA), Paseo de Miramón 194, 20014, Donostia San Sebastián, Spain Basque Fdn Sci, Ikerbasque, 48013 Bilbao, Spain 10.3762/bjoc.19.42 Abstract A light-driven metal-free protocol for the synthesis of sulfone-containing indoles under mild conditions is reported. Specifically
  • halogen-bonded EDA complex (Ia) between the sulfone 2a and DABCO (Figure 4). When irradiated, this photoactive aggregate led to the formation of reactive alkyl radicals (IIa), which may react with indole 1a eventually yielding the product 3a through a classical HAS pathway [31][32][33]. Then, we
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Published 27 Apr 2023

Transition-metal-catalyzed C–H bond activation as a sustainable strategy for the synthesis of fluorinated molecules: an overview

  • Louis Monsigny,
  • Floriane Doche and
  • Tatiana Besset

Beilstein J. Org. Chem. 2023, 19, 448–473, doi:10.3762/bjoc.19.35

Graphical Abstract
  • corresponding sulfoxide and the sulfone was possible and the corresponding products were obtained in 98% and 95% yields, respectively. This reaction was successfully expanded to the trifluoromethylthiolation of derivatives bearing various directing groups such as substituted pyridines (4 examples, up to 84
  • approach. Of high interest, the modularity of the SCF2CO2Et was highlighted by its conversion into various other fluorinated residues (amide, carboxylic acid) and its selective oxidation into the corresponding sulfoxide and sulfone. I.5) Trifluoromethylselenolation of aromatic and vinylic C(sp2)–H bonds by
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Published 17 Apr 2023

Combretastatins D series and analogues: from isolation, synthetic challenges and biological activities

  • Jorge de Lima Neto and
  • Paulo Henrique Menezes

Beilstein J. Org. Chem. 2023, 19, 399–427, doi:10.3762/bjoc.19.31

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  • synthesis of combretastatin D-1 (1) using the flash vacuum pyrolysis (FVP) technique, which consisted on the contraction of 16-membered sulfone derivatives, by extrusion of sulfur dioxide [58]. The synthesis of the required sulfone was initiated by a Horner–Wadsworth–Emmons reaction between the aldehyde 52
  • sulfone 134 using m-CPBA [63] followed by contraction of the macrocyclic ring by extrusion of SO2 using FVP gave compound 28 together with macrocycle 135, obtained from the simultaneous extrusion of SO2 and CO2. Cleavage of the methyl ether in 28 gave the desired product 2 in 0.6% overall yield after 10
  • macrocyclization using SO3·pyridine [68] gave the corresponding thioether 151, which was oxidized to the cyclic sulfone 152 using m-CPBA. Extrusion of SO2 by FVP followed by demethylation of the formed macrolide furnished the compound 154 which can be converted in combretastatin D-1 (1) by known methodologies [43
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Published 29 Mar 2023

Redox-active molecules as organocatalysts for selective oxidative transformations – an unperceived organocatalysis field

  • Elena R. Lopat’eva,
  • Igor B. Krylov,
  • Dmitry A. Lapshin and
  • Alexander O. Terent’ev

Beilstein J. Org. Chem. 2022, 18, 1672–1695, doi:10.3762/bjoc.18.179

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  • that hydrogen bonding is considered as one of the key factors determining the selectivity of catalyst-free sulfoxidations [68]. In such reactions, the selectivity of sulfide oxidation by oxone (sulfoxide/sulfone ratio) was controlled by the solvent nature (deeper oxidation was observed in water than in
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Published 09 Dec 2022

B–N/B–H Transborylation: borane-catalysed nitrile hydroboration

  • Filip Meger,
  • Alexander C. W. Kwok,
  • Franziska Gilch,
  • Dominic R. Willcox,
  • Alex J. Hendy,
  • Kieran Nicholson,
  • Andrew D. Bage,
  • Thomas Langer,
  • Thomas A. Hunt and
  • Stephen P. Thomas

Beilstein J. Org. Chem. 2022, 18, 1332–1337, doi:10.3762/bjoc.18.138

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  • relies upon stoichiometric reagents or transition-metal catalysis. Herein, a borane-catalysed hydroboration of nitriles to give primary amines is reported. Good yields (48–95%) and chemoselectivity (e.g., ester, nitro, sulfone) were observed. DFT calculations and mechanistic studies support the proposal
  • %), nitro (1r, 67%), and sulfone (1s, 48%). The 1H NMR spectra of the crude reaction mixtures displayed no reduction of these functional groups. Such functional group tolerance was not exhibited by the other non-metal and boron-based catalytic nitrile hydroboration systems [22][23][24][27]. It should be
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Published 26 Sep 2022

Ionic multiresonant thermally activated delayed fluorescence emitters for light emitting electrochemical cells

  • Merve Karaman,
  • Abhishek Kumar Gupta,
  • Subeesh Madayanad Suresh,
  • Tomas Matulaitis,
  • Lorenzo Mardegan,
  • Daniel Tordera,
  • Henk J. Bolink,
  • Sen Wu,
  • Stuart Warriner,
  • Ifor D. Samuel and
  • Eli Zysman-Colman

Beilstein J. Org. Chem. 2022, 18, 1311–1321, doi:10.3762/bjoc.18.136

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  • the non-doped device, at 2.0% demonstrated 100% exciton utilization efficiency in the device and efficient energy transfer from the host to the guest cyanine emitter. Deep blue emission in LEECs is challenging. We also reported a blue-emitting LEEC employing a cationic sulfone-based donor–acceptor
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Published 22 Sep 2022

A one-pot electrochemical synthesis of 2-aminothiazoles from active methylene ketones and thioureas mediated by NH4I

  • Shang-Feng Yang,
  • Pei Li,
  • Zi-Lin Fang,
  • Sen Liang,
  • Hong-Yu Tian,
  • Bao-Guo Sun,
  • Kun Xu and
  • Cheng-Chu Zeng

Beilstein J. Org. Chem. 2022, 18, 1249–1255, doi:10.3762/bjoc.18.130

Graphical Abstract
  • protocol proceeds in an undivided cell equipped with graphite plate electrodes under constant current conditions. Various active methylene ketones, including β-keto ester, β-keto amide, β-keto nitrile, β-keto sulfone and 1,3-diketones, can be converted to the corresponding 2-aminothiazoles. Mechanistically
  • 3v in 23% yield. In addition to β-keto esters, other active methylene derivatives, including β-ketoamide, β-keto nitrile and β-keto sulfone were also suitable coupling partners with relatively lower yields (3w–y) and most of the starting materials were recovered. The method could also be applied to
  • performed in an undivided cell with NH4I as the mediator and cheap graphite plate as the working electrode. Various active methylene ketones, including β-keto ester, β-keto amide, β-keto nitrile, β-keto sulfone and 1,3-diones proved to be compatible with the protocol. Since external oxidants and
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Published 15 Sep 2022

Synthetic strategies for the preparation of γ-phostams: 1,2-azaphospholidine 2-oxides and 1,2-azaphospholine 2-oxides

  • Jiaxi Xu

Beilstein J. Org. Chem. 2022, 18, 889–915, doi:10.3762/bjoc.18.90

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  • ethyl and butyl acrylates, but-3-en-2-one, N,N-dimethylacrylamide, acrylonitrile, and phenyl vinyl sulfone. In addition, ethyl 1-arylvinyl-N-phenylphosphonamidates 246 were able to react with methyl acrylate (241), affording methyl 2-(3-aryl-2-ethoxy-2-oxo-1-phenyl-1,5-dihydro-1,2-azaphosphol-5-yl
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Published 22 Jul 2022

Synthesis of α-(perfluoroalkylsulfonyl)propiophenones: a new set of reagents for the light-mediated perfluoroalkylation of aromatics

  • Durbis J. Castillo-Pazos,
  • Juan D. Lasso and
  • Chao-Jun Li

Beilstein J. Org. Chem. 2022, 18, 788–795, doi:10.3762/bjoc.18.79

Graphical Abstract
  • generated in situ from propiophenone, and second, the deprotection of propiophenone α-thioesters in the presence of perfluoroalkyliodides and subsequent oxidation of the formed perfluorothioether into the sulfone. However, none of these proposed pathways gave yields high enough for the reaction to be
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Published 04 Jul 2022

Substituent effect on TADF properties of 2-modified 4,6-bis(3,6-di-tert-butyl-9-carbazolyl)-5-methylpyrimidines

  • Irina Fiodorova,
  • Tomas Serevičius,
  • Rokas Skaisgiris,
  • Saulius Juršėnas and
  • Sigitas Tumkevicius

Beilstein J. Org. Chem. 2022, 18, 497–507, doi:10.3762/bjoc.18.52

Graphical Abstract
  • such as triazine, diazines or aromatics containing cyano and sulfone groups are popular acceptor units for the construction of highly efficient TADF emitters [8][9][10][11]. Pyrimidine (1,3-diazine) owing to its aromaticity, significant π-deficiency, strong electron affinity, high luminous efficiency
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Published 05 May 2022

DABCO-promoted photocatalytic C–H functionalization of aldehydes

  • Bruno Maia da Silva Santos,
  • Mariana dos Santos Dupim,
  • Cauê Paula de Souza,
  • Thiago Messias Cardozo and
  • Fernanda Gadini Finelli

Beilstein J. Org. Chem. 2021, 17, 2959–2967, doi:10.3762/bjoc.17.205

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  • was the study of the aldehyde scope, using 4-bromophenyl methyl sulfone as a coupling partner. We were delighted to see that both aliphatic and aromatic aldehydes could be arylated using this protocol with good to excellent yields (13–16, 69–89%), although 4-anisaldehyde led to a diminished yield when
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Published 21 Dec 2021

Selective sulfonylation and isonitrilation of para-quinone methides employing TosMIC as a source of sulfonyl group or isonitrile group

  • Chuanhua Qu,
  • Run Huang,
  • Yong Li,
  • Tong Liu,
  • Yuan Chen and
  • Guiting Song

Beilstein J. Org. Chem. 2021, 17, 2822–2831, doi:10.3762/bjoc.17.193

Graphical Abstract
  • diarylmethyl sulfone 3e. The chemistry of TosMIC in the reactions with olefins. ZnI2-catalyzed C–S-bond cleavage of TosMIC for the synthesis of diarylmethyl sulfones 3a–m. Reaction conditions unless otherwise specified: 1 (0.2 mmol), 2a (0.4 mmol), ZnI2 (0.04 mmol), Cs2CO3 (0.4 mmol), THF (1.0 mL), MW 90 °C
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Published 02 Dec 2021

Recent advances in the tandem annulation of 1,3-enynes to functionalized pyridine and pyrrole derivatives

  • Yi Liu,
  • Puying Luo,
  • Yang Fu,
  • Tianxin Hao,
  • Xuan Liu,
  • Qiuping Ding and
  • Yiyuan Peng

Beilstein J. Org. Chem. 2021, 17, 2462–2476, doi:10.3762/bjoc.17.163

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  • , agrochemical, and organic synthetic chemistry. For example, 5-selenyl- and 5-sulfenyl-appended nicotinates 18c and 19c could be oxidized by mCPBA to the corresponding selenoxide, sulfoxide, and sulfone derivatives 22, 24, and 25, respectively. In addition, 5‑selenyl-substituted nicotinate 18c could be
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Published 22 Sep 2021

Allylic alcohols and amines by carbenoid eliminative cross-coupling using epoxides or aziridines

  • Matthew J. Fleming and
  • David M. Hodgson

Beilstein J. Org. Chem. 2021, 17, 2385–2389, doi:10.3762/bjoc.17.155

Graphical Abstract
  • ). Access to allylic alcohol 8 was also achievable (55%, E/Z = 56:44) in a tin-free process using a sulfonyl leaving group, via α-lithiation of sulfone 15 [18] and in the presence of LTMP (Scheme 7). γ-Hydroxysulfone 16 was formed competitively (44%, dr = 50:50), by direct addition of the lithiated sulfone
  • epoxide 5. Synthesis of vinylsilane 14. Allylic alcohol 8 from epoxide 5 and sulfone 15. Allylic amines from aziridine 17. Cyclopropylidene synthesis from aziridine 20. Cinnamylamine 23 synthesis from aziridine 17. Cinnamylamine 23 synthesis from isopropyl or neopentyl benzylic ethers 26 and 27
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Published 10 Sep 2021

Electron-rich triarylphosphines as nucleophilic catalysts for oxa-Michael reactions

  • Susanne M. Fischer,
  • Simon Renner,
  • A. Daniel Boese and
  • Christian Slugovc

Beilstein J. Org. Chem. 2021, 17, 1689–1697, doi:10.3762/bjoc.17.117

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  • triarylphosphines TPP, MMTPP and TMTPP as catalysts for the oxa-Michael reaction three varyingly strong Michael acceptors, namely acrylonitrile (1), acrylamide (2) and divinyl sulfone (3) were reacted with four different alcohols of similar molecular mass but different acidity (Figure 1). The stoichiometry of
  • , the difunctional divinyl sulfone was tested as the strongest Michael acceptor (E = −18.36, for phenyl vinyl sulfone [19]) under investigation. In distinction from the experiments described above, three equivalents of the alcohol were used. In general, the different catalysts perform very similar in
  • this reaction giving high double-bond conversions of about 80% after already 1 h [26]. A mixture of mono- (3monoa–d) and di-adducts (3dia–d) are observed and only in case of 2-propanol also divinyl sulfone is still present. With 2-propanol a slight but significant influence of the catalyst choice on
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Published 21 Jul 2021

A comprehensive review of flow chemistry techniques tailored to the flavours and fragrances industries

  • Guido Gambacorta,
  • James S. Sharley and
  • Ian R. Baxendale

Beilstein J. Org. Chem. 2021, 17, 1181–1312, doi:10.3762/bjoc.17.90

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Published 18 May 2021

Synthetic reactions driven by electron-donor–acceptor (EDA) complexes

  • Zhonglie Yang,
  • Yutong Liu,
  • Kun Cao,
  • Xiaobin Zhang,
  • Hezhong Jiang and
  • Jiahong Li

Beilstein J. Org. Chem. 2021, 17, 771–799, doi:10.3762/bjoc.17.67

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  • of N-heterocyclic compounds. In 2017, Wu and colleagues [58] uncovered the use of the bis(sulfur dioxide) adduct of DABCO, 1,4-diazabicyclo[2.2.2]octane·(SO2)2, as sulfone source in the EDA complex formation by 4-methyl-1-(p-tolyl)pentan-1-one O-(2,4-dinitrophenyl)oxime (11) towards the
  • trifluoromethyl alkynylation product 84 with alkynyl sulfone 83, alkene 81, and Togni reagent 82 as substrates catalyzed by 2,4,6-trimethylpyridine (TMP). The EDA complex formed by electron donor TMP and electron acceptor Togni reagent 82 facilitated electron transfer, yielding trifluoromethyl radical to initiate
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Published 06 Apr 2021
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  • , which have potent activity against breast cancer. The easy access to the corresponding sulfones presents a versatile route for the implementation of a new biologically active moiety, the sulfone, to the β-naphthyl-β-sulfanyl ketones. The enantioenriched products of both classes can be evaluated as
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Published 18 Feb 2021

Synthetic approaches to bowl-shaped π-conjugated sumanene and its congeners

  • Shakeel Alvi and
  • Rashid Ali

Beilstein J. Org. Chem. 2020, 16, 2212–2259, doi:10.3762/bjoc.16.186

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Published 09 Sep 2020

Isolation and structure determination of a tetrameric sulfonyl dilithio methandiide in solution based on crystal structure analysis and 6Li/13C NMR spectroscopic data

  • Jürgen Vollhardt,
  • Hans Jörg Lindner and
  • Hans-Joachim Gais

Beilstein J. Org. Chem. 2020, 16, 2057–2063, doi:10.3762/bjoc.16.172

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  • substructure of which could be disclosed [15]. We describe in this paper the isolation of a tetramer of 2a and the determination of its structure in solution based on crystal structure analysis and previously described NMR spectroscopic data. Results and Discussion Crystal structure Treatment of sulfone 4 in a
  • (2a)4·(THF)6 are in the range of those found in the hexamer (2a)6·Li2O·(THF)6 and functionalized dilithio sulfonyl methandiides [40][43]. Solution structure The synthesis of 2a from sulfone 6Li and 13C-labelled 4 with Li2O-free n-BuLi had yielded the methandiide, being readily soluble in THF. 13C and
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Published 21 Aug 2020

Syntheses of spliceostatins and thailanstatins: a review

  • William A. Donaldson

Beilstein J. Org. Chem. 2020, 16, 1991–2006, doi:10.3762/bjoc.16.166

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  • oxidation stereoselectively generated the spirocyclic epoxide 76. A second-protecting group shuffle afforded the primary alcohol 77. A Mitsunobu substitution of 77 with 2-mercaptobenzothiazole, followed by an oxidation with a large excess of mCPBA afforded the sulfone 78. While not producing the identical
  • afforded the fragment 125. The cross-metathesis of 125 with an excess of methacrolein in the presence of the Ru catalyst 122 gave the aldehyde 126. This coupling is analogous to Koide’s cross-metathesis of 121 (cf. Scheme 20). A modified Julia olefination of 126 with the anion generated from the sulfone 78
  • , followed by the cleavage of the 4’-TBS protecting group gave 127 in an acceptable yield (52%). A protecting-group adjustment finalized the synthesis of 124. Notably, these authors found that switching the sulfone and aldehyde functionalities, i.e., an olefination of the aldehyde generated by the oxidation
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Published 13 Aug 2020

Synthesis, docking study and biological evaluation of ᴅ-fructofuranosyl and ᴅ-tagatofuranosyl sulfones as potential inhibitors of the mycobacterial galactan synthesis targeting the galactofuranosyltransferase GlfT2

  • Marek Baráth,
  • Jana Jakubčinová,
  • Zuzana Konyariková,
  • Stanislav Kozmon,
  • Katarína Mikušová and
  • Maroš Bella

Beilstein J. Org. Chem. 2020, 16, 1853–1862, doi:10.3762/bjoc.16.152

Graphical Abstract
  • investigations on their more stable analogs resulted in the synthesis of stable 1-O-phoshono-β-ᴅ-psicofuranosyl sulfone, which was prepared by a simultaneous phosphorylation and oxidation of ethyl 2-thio-β-ᴅ-psicofuranoside with dibenzyl N,N-dimethylphosphoramidite catalyzed by 1H-tetrazole and followed by
  • thiol from exo-face of the bicyclic skeleton. Subsequent simultaneous phosphorylation and oxidation of ethyl 2-thio-ᴅ-tagatofuranoside 13 under identical conditions as used for the fructofuranose pathway provided 1-O-dibenzyloxyphosphoryl-ᴅ-tagatofuranosyl sulfone 14 (Scheme 3). Removal of the pivaloyl
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Published 27 Jul 2020

Pauson–Khand reaction of fluorinated compounds

  • Jorge Escorihuela,
  • Daniel M. Sedgwick,
  • Alberto Llobat,
  • Mercedes Medio-Simón,
  • Pablo Barrio and
  • Santos Fustero

Beilstein J. Org. Chem. 2020, 16, 1662–1682, doi:10.3762/bjoc.16.138

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  • testing a variety of reaction conditions. More complex biorelevant examples such as isatin derivatives were also suitable substrates, affording the corresponding spirocyclic derivatives, albeit in low yields (Scheme 21) [59]. Unfortunately, thioether and sulfone-based linkers were unsuitable in this
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Published 14 Jul 2020

Heterogeneous photocatalysis in flow chemical reactors

  • Christopher G. Thomson,
  • Ai-Lan Lee and
  • Filipe Vilela

Beilstein J. Org. Chem. 2020, 16, 1495–1549, doi:10.3762/bjoc.16.125

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  • (Figure 11) [129]. Four conjugated polymers containing dibenzothiophene sulfone (FSO) monomers, linked by either biphenyl (FSO-BP), fluorene (FSO-F), 2,8-dibenzothiophene (FSO-FSz), or 3,7-dibenzothiophene (FSO-FS) monomers were synthesised and applied in the photocatalytic hydrogen evolution reaction
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Published 26 Jun 2020

Photocatalysis with organic dyes: facile access to reactive intermediates for synthesis

  • Stephanie G. E. Amos,
  • Marion Garreau,
  • Luca Buzzetti and
  • Jerome Waser

Beilstein J. Org. Chem. 2020, 16, 1163–1187, doi:10.3762/bjoc.16.103

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Published 29 May 2020
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