Improved deconvolution of natural products’ protein targets using diagnostic ions from chemical proteomics linkers

• Andreas Wiest and
• Pavel Kielkowski

Beilstein J. Org. Chem. 2024, 20, 2323–2341, doi:10.3762/bjoc.20.199

• proteins can be proteolytically cleaved on-beads or directly eluted for further enrichment on an affinity resin. Due to the easy handling of the magnetic beads and separation for the liquid phase using the magnet, the protocol utilizing the carboxylate magnetic beads was first developed for whole proteome

1,2-Difluoroethylene (HFO-1132): synthesis and chemistry

• Liubov V. Sokolenko,
• Taras M. Sokolenko and
• Yurii L. Yagupolskii

Beilstein J. Org. Chem. 2024, 20, 1955–1966, doi:10.3762/bjoc.20.171

• converted into polyfluorinated olefins RFCF=CFH by HI elimination. Cyclization reactions Carbocyclizations: A series of articles devoted to structural investigations of 1,2-difluorocyclopropanes was published [96][97][98]. For this purpose, cis- and trans-1,2-difluorocyclopropanes were synthesized by liquid

• -phase photolysis at −80 °C from 1,2-difluoroethylene and diazomethane (Scheme 19). Unfortunately, the product yield was not reported. Diels–Alder reaction of (E)- and (Z)-1,2-difluoroethylenes with hexachlorocyclopentadiene was studied by Ihrid and Smith [99]. It was shown that (Z)-1,2-difluoroethylene

Synthesis of substituted triazole–pyrazole hybrids using triazenylpyrazole precursors

• Simone Gräßle,
• Laura Holzhauer,
• Nicolai Wippert,
• Olaf Fuhr,
• Martin Nieger,
• Nicole Jung and
• Stefan Bräse

Beilstein J. Org. Chem. 2024, 20, 1396–1404, doi:10.3762/bjoc.20.121

• (14b) was immobilized on benzylamine resin 22 (Scheme 5). For this purpose, a diazonium intermediate was generated from the pyrazoloamine with BF3∙Et2O and isoamyl nitrite accordingly to the liquid phase synthesis of 15b. The subsequent functionalization of resin 23 to the phenyl-substituted derivative

• achieved with a total yield of 37% over all steps, comparable to the total yield of 45% for the stepwise synthesis in the liquid phase. This indicates a material loss due to the non-reactive regioisomer formation in the previous step and a non-quantitative cleavage process. In analogy to the one-pot

Optimizing reaction conditions for the light-driven hydrogen evolution in a loop photoreactor

• Pengcheng Li,
• Daniel Kowalczyk,
• Johannes Liessem,
• Mohamed M. Elnagar,
• Dariusz Mitoraj,
• Radim Beranek and
• Dirk Ziegenbalg

Beilstein J. Org. Chem. 2024, 20, 74–91, doi:10.3762/bjoc.20.9

• ) processes, and photocatalysis. Upon upscaling, both PV-E and PEC reactors exhibit pH gradients at electrodes and elevated solution electrical resistivity. These challenges arise from the substantial separation between reduction and oxidation sites, alongside mass transport restrictions in the liquid phase

• maximum hydrogen generation rate was 1.5 times higher at 740 rpm than at 430 rpm. This gives evidence that increased convection improves the mass transfer of generated hydrogen from the liquid phase to the gas phase or even directly from the catalyst to the gas phase. This is in line with the measured

Charge carrier transport in perylene-based and pyrene-based columnar liquid crystals

• Alessandro L. Alves,
• Simone V. Bernardino,
• Carlos H. Stadtlober,
• Edivandro Girotto,
• Giliandro Farias,
• Rodney M. do Nascimento,
• Sergio F. Curcio,
• Thiago Cazati,
• Marta E. R. Dotto,
• Juliana Eccher,
• Leonardo N. Furini,
• Hugo Gallardo,
• Harald Bock and
• Ivan H. Bechtold

Beilstein J. Org. Chem. 2023, 19, 1755–1765, doi:10.3762/bjoc.19.128

• the autofocus. XRD measurements were performed with an X’Pert PRO (PANalytical) diffractometer using Cu Kα radiation (λ = 1.5418 Å) equipped with an X’Celerator detector. A small amount of 1 or 2 was deposited onto a glass substrate and heated to the isotropic liquid phase. The diffracted radiation

Radical chemistry in polymer science: an overview and recent advances

• Zixiao Wang,
• Feichen Cui,
• Yang Sui and
• Jiajun Yan

Beilstein J. Org. Chem. 2023, 19, 1580–1603, doi:10.3762/bjoc.19.116

• dissolved initiators in the liquid phase during the process. A suspending agent, e.g., polyvinyl alcohol (PVA), is added to the system to prevent coalescence. The viscosity in suspension polymerization is low throughout the process which brings good heat transfer and temperature control, and therefore well

Two new lanostanoid glycosides isolated from a Kenyan polypore Fomitopsis carnea

• Winnie Chemutai Sum,
• Sherif S. Ebada,
• Didsanutda Gonkhom,
• Cony Decock,
• Rémy Bertrand Teponno,
• Josphat Clement Matasyoh and
• Marc Stadler

Beilstein J. Org. Chem. 2023, 19, 1161–1169, doi:10.3762/bjoc.19.84

• reversed-phase HPLC system (PLC 2020; Gilson, Middleton, WI, USA), equipped with a VP Nucleodur 100-5 C-18 ec packed column (25 × 40 mm, 7 μm, Macherey-Nagel) as stationary phase. The liquid phase consisted of solvent A and solvent B. The elution gradients for the Q6/2 and rice extracts were identical and

Honeycomb reactor: a promising device for streamlining aerobic oxidation under continuous-flow conditions

• Masahiro Hosoya,
• Yusuke Saito and
• Yousuke Horiuchi

Beilstein J. Org. Chem. 2023, 19, 752–763, doi:10.3762/bjoc.19.55

• -tube reactors or fixed bed reactors [17][18][19][20]. To maximize this advantage, the gas–liquid biphasic reaction must be controlled under continuous-flow conditions. This reaction requires high mixing efficiency to assure high mass transfer of the gas to the liquid phase and a consequent high

Mechanochemical solid state synthesis of copper(I)/NHC complexes with K₃PO₄

• Ina Remy-Speckmann,
• Birte M. Zimmermann,
• Mahadeb Gorai,
• Martin Lerch and
• Johannes F. Teichert

Beilstein J. Org. Chem. 2023, 19, 440–447, doi:10.3762/bjoc.19.34

• the standard reactions for catalytic hydrogenations with copper(I)/NHC complexes [4]. In this vein, we tested complex 5 from solid and liquid phase synthesis in the catalytic hydrogenation of esters, carbonyl compounds and in the semihydrogenation of alkynes. In the catalytic hydrogenation of ethyl

Investigation of cationic ring-opening polymerization of 2-oxazolines in the “green” solvent dihydrolevoglucosenone

• Solomiia Borova and
• Robert Luxenhofer

Beilstein J. Org. Chem. 2023, 19, 217–230, doi:10.3762/bjoc.19.21

• trifluoromethanesulfonate (2.38 g, 14.50 mmol, 1.2 equiv) was added. The mixture was cooled in an ice bath. Then, 2-ethyl-2-oxazoline (1.20 g, 12.10 mmol, 1.0 equiv) was added slowly. A slight turbidity of the solution was observed. Over time an oily and colorless liquid phase was formed. The diethyl ether phase was

Preparation of β-cyclodextrin/polysaccharide foams using saponin

• Max Petitjean and
• José Ramón Isasi

Beilstein J. Org. Chem. 2023, 19, 78–88, doi:10.3762/bjoc.19.7

• the emulsion production needs to be followed quickly by the freezing of the foam, otherwise a continuous liquid phase could be formed prior to the lyophilization process. The two chitosan solutions, with or without cyclodextrin, produce foams with similar stabilities. On the other hand, the presence

Improving the accuracy of ³¹P NMR chemical shift calculations by use of scaling methods

• William H. Hersh and
• Tsz-Yeung Chan

Beilstein J. Org. Chem. 2023, 19, 36–56, doi:10.3762/bjoc.19.4

• actual use of this compound requires a fairly extraordinary experimental setup [52][53]. An additional issue with PH3 involves the choice of using the gas-phase or liquid-phase experimental chemical shifts, which differ dramatically: the universally used value for the gas-phase chemical shift is −266.1

• ppm (referenced to external 85% H3PO4) [54], while the liquid-phase chemical shift is −238 ppm at −90 °C [44] and is also −238 ppm at 23 °C in CCl4 [52]. In the two 31P NMR studies described in the Introduction, Latypov used the gas-phase value [37] and Krivdin the liquid-phase value [24]. As noted

• worse fit (MAD/RMSD = 8.5/11.6 ppm vs the 7.8/9.7 ppm shown for the −238 ppm liquid-phase value shown). Since the absolute shielding of the reference (here σ(H3PO4)calcd) is a constant, one can equally well create a scaling equation using just the experimental vs the calculated absolute shieldings by

Inline purification in continuous flow synthesis – opportunities and challenges

• Jorge García-Lacuna and
• Marcus Baumann

Beilstein J. Org. Chem. 2022, 18, 1720–1740, doi:10.3762/bjoc.18.182

• optimization of such autonomous processes. A desirable feature of these membranes is that they can be applied in syntheses where all the impurities remain in one liquid phase while the desired product resides in the other liquid phase which means that the downstream step consists of offline solvent evaporation

• applications by synthetic chemists include porous capillary separators to separate different mixtures of organic and aqueous solvents [65], a concentric annular liquid–liquid phase separation approach for continuous processing [66] and a single-stage extraction device based on a vertical apparatus with

Rapid gas–liquid reaction in flow. Continuous synthesis and production of cyclohexene oxide

• Kyoko Mandai,
• Tetsuya Yamamoto,
• Hiroki Mandai and
• Aiichiro Nagaki

Beilstein J. Org. Chem. 2022, 18, 660–668, doi:10.3762/bjoc.18.67

• stainless steel parts and devices. This continuous-flow process demonstrates a significant improvement in reaction time for highly selective epoxide production over the batch process due to the efficient mass transfer between the liquid phase and air. The flow process discovered was operated continuously

Menadione: a platform and a target to valuable compounds synthesis

• Acácio S. de Souza,
• Ruan Carlos B. Ribeiro,
• Dora C. S. Costa,
• Fernanda P. Pauli,
• David R. Pinho,
• Matheus G. de Moraes,
• Fernando de C. da Silva,
• Luana da S. M. Forezi and
• Vitor F. Ferreira

Beilstein J. Org. Chem. 2022, 18, 381–419, doi:10.3762/bjoc.18.43

• ]. Selvaraj and co-workers reported the liquid-phase oxidation of 17 using Ti-containing mesoporous silica catalysts, TiSBA-15 (Table 2, entry 3) [67]. According to the authors, the best result was achieved with TiSBA-15 (nSi/nTi = 6) catalysis and H2O2, exhibiting 93% selectivity to menadione (10). In

• addition, catalyst recycling experiments showed the TiSBA-15(6) had higher catalytic stability in the liquid-phase oxidation as compared to other titanium-containing mesoporous catalysts [67]. Cavani and co-workers reported a heterogenous catalyst system for the oxidation of 2-methylnaphthol (17) using 35

• % aqueous H2O2 and niobium oxide dispersed in silica (Nb2O2-SiO2) as catalyst (Table 2, entry 4) to obtain menadione (10) in 60% yield [68]. Another approach using niobium was developed by the Selvaraj group, which used mesoporous NbSBA-15 catalysts in the liquid-phase oxidation of 17 (Table 2, entry 5) [69

High-speed C–H chlorination of ethylene carbonate using a new photoflow setup

• Takayoshi Kasakado,
• Takahide Fukuyama,
• Tomohiro Nakagawa,
• Shinji Taguchi and
• Ilhyong Ryu

Beilstein J. Org. Chem. 2022, 18, 152–158, doi:10.3762/bjoc.18.16

• chloroethylene carbonate, a precursor to vinylene carbonate. A novel photoflow setup designed for a gas–liquid biphasic reaction turned out to be useful for the direct use of chlorine gas. The setup employed sloped channels so as to make the liquid phase thinner, ensuring a high surface-to-volume ratio. When

First total synthesis of hoshinoamide A

• Haipin Zhou,
• Zihan Rui,
• Yiming Yang,
• Shengtao Xu,
• Yutian Shao and
• Long Liu

Beilstein J. Org. Chem. 2021, 17, 2924–2931, doi:10.3762/bjoc.17.201

• -sensitive Plasmodium falciparum. Herein, we describe the first total synthesis of hoshinoamide A by the combination of liquid-phase and solid-phase peptide synthesis. Liquid-phase synthesis is to improve the coupling yield of ʟ-Val3 and N-Me-ᴅ-Phe2. Connecting other amino acids efficiency and convergence is

• of the malaria parasites (IC50 = 0.96 μM) and African sleeping sickness (IC50 = 2.9 μM). Hoshinoamide C was firstly synthesized from Boc-protected amino acids in liquid phase [12]. Both hoshinoamides A and B are highly methylated polypeptides containing three N-methyl amino acids: N-Me-ʟ-Leu7, N-Me-ᴅ

• synthesized in high efficiency. After systematic screening of the coupling reagents in liquid phase, the key intermediate tripeptide 7 was obtained in high yield. The solid-phase synthesis improves the entire efficiency of the synthetic route. This strategy could be applied to the stereoselective synthesis of

Recent advances in organocatalytic asymmetric aza-Michael reactions of amines and amides

• Pratibha Sharma,
• Raakhi Gupta and
• Raj K. Bansal

Beilstein J. Org. Chem. 2021, 17, 2585–2610, doi:10.3762/bjoc.17.173

• ) in the presence of cesium carbonate and an N-benzylquininium salt as catalyst (cat. 48) (solid–liquid phase-transfer conditions) to give the corresponding adducts in 40–90% yields with excellent ee of up to 99% (Table 10) [44]. A different type of asymmetric aza-Michael addition was developed by Wang

Exfoliated black phosphorous-mediated CuAAC chemistry for organic and macromolecular synthesis under white LED and near-IR irradiation

• Azra Kocaarslan,
• Zafer Eroglu,
• Önder Metin and
• Yusuf Yagci

Beilstein J. Org. Chem. 2021, 17, 2477–2487, doi:10.3762/bjoc.17.164

• sonicated crystals were carefully transferred to a Schlenk tube and dried under vacuum. The Schlenk tube was filled with argon and crushed under inert atmosphere. The produced BP crystals were stored under vacuum. BP nanosheets were prepared by the liquid phase exfoliation of BP crystals. A specific amount

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

Amine–borane complex-initiated SF₅Cl radical addition on alkenes and alkynes

• Audrey Gilbert,
• Pauline Langowski,
• Marine Delgado,
• Laurent Chabaud,
• Mathieu Pucheault and
• Jean-François Paquin

Beilstein J. Org. Chem. 2020, 16, 3069–3077, doi:10.3762/bjoc.16.256

• liquid phase (SF5Cl being a gas that boils at −21 °C) in milder reaction conditions and in normal glassware, instead of using special apparatus such as autoclaves and photochemical reactors [31]. Moreover, this method leads to significantly higher yields in shorter reaction times compared to the previous

Secondary metabolites of Bacillus subtilis impact the assembly of soil-derived semisynthetic bacterial communities

• Heiko T. Kiesewalter,
• Carlos N. Lozano-Andrade,
• Mikael L. Strube and
• Ákos T. Kovács

Beilstein J. Org. Chem. 2020, 16, 2983–2998, doi:10.3762/bjoc.16.248

• for 15 min, and allowed to sediment for 2 min. Four independent communities were established by inoculating 10-times diluted TSB (0.1 × TSB) with 1% soil suspension taken from the middle part of the liquid phase, followed by incubation at 21–23 °C and 250 rpm for 12 h. Simultaneously, pregrown B

Dawn of a new era in industrial photochemistry: the scale-up of micro- and mesostructured photoreactors

• Emine Kayahan,
• Mathias Jacobs,
• Leen Braeken,
• Leen C.J. Thomassen,
• Simon Kuhn,
• Tom van Gerven and
• M. Enis Leblebici

Beilstein J. Org. Chem. 2020, 16, 2484–2504, doi:10.3762/bjoc.16.202

• of the photocatalytic oxidation of thiophenol to phenyl disulfide using a Taylor flow in a microreactor that consists of a capillary tube. By varying the flow rate of the gas and liquid phase and comparing the oxygen concentration in the liquid phase with the equilibrium concentration without a

Clickable azide-functionalized bromoarylaldehydes – synthesis and photophysical characterization

• Dominik Göbel,
• Marius Friedrich,
• Enno Lork and
• Boris J. Nachtsheim

Beilstein J. Org. Chem. 2020, 16, 1683–1692, doi:10.3762/bjoc.16.139

• non-radiative transitions can be achieved by the host–guest method [50][51][52] or by crystallization [53][54][55][56][57]. In difference to the liquid phase, the highly ordered packing and the restriction of molecular motions in the crystalline state favor a persistent luminescence. The promotion of

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