Anion exchange resins in phosphate form as versatile carriers for the reactions catalyzed by nucleoside phosphorylases

• Julia N. Artsemyeva,
• Ekaterina A. Remeeva,
• Tatiana N. Buravskaya,
• Irina D. Konstantinova,
• Roman S. Esipov,
• Anatoly I. Miroshnikov,
• Natalia M. Litvinko and
• Igor A. Mikhailopulo

Beilstein J. Org. Chem. 2020, 16, 2607–2622, doi:10.3762/bjoc.16.212

• -catalyzed oxidation of the hypoxanthine formed to uric acid [40] and H2O2, and the latter was converted to H2O and oxygen by catalase preventing thereby the reverse formation of the starting Ino. The Rib-1Pi (2Na+) was isolated from the reaction mixture in 74% yield (32 IU of PNP per 1 mmol of Ino; 50 mM Na

Synthesis of novel fluorinated building blocks via halofluorination and related reactions

• Attila Márió Remete,
• Tamás T. Novák,
• Melinda Nonn,
• Matti Haukka,
• Ferenc Fülöp and
• Loránd Kiss

Beilstein J. Org. Chem. 2020, 16, 2562–2575, doi:10.3762/bjoc.16.208

• (rac)-33 formed primarily (Scheme 22). A possible driving force of this reaction is the extended conjugation. Interestingly, the treatment of a mixture of (rac)-31 with H2O2/CF3COOH resulted in single allylic fluoride, (rac)-35 (Scheme 23). Unfortunately, the determination of the stereochemistry via

The B & B approach: Ball-milling conjugation of dextran with phenylboronic acid (PBA)-functionalized BODIPY

• Patrizia Andreozzi,
• Lorenza Tamberi,
• Elisamaria Tasca,
• Gina Elena Giacomazzo,
• Marta Martinez,
• Mirko Severi,
• Marco Marradi,
• Stefano Cicchi,
• Sergio Moya,
• Giacomo Biagiotti and
• Barbara Richichi

Beilstein J. Org. Chem. 2020, 16, 2272–2281, doi:10.3762/bjoc.16.188

• accurately weighted amount of each sample was treated with a microwave-assisted digestion (CEM MARS Xpress) using 1 mL of suprapure HNO3 obtained by sub-boiling distillation and 1 mL of suprapure H2O2. Each sample was thus diluted to 10 mL with Ultrapure water (UHQ), spiked with 0.5 ppm of Ge used as an

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

• generate the corresponding pyrazine-fused sumanene networks 169a–f and 170a–f in low-to-good yields (Scheme 44). As can be inspected from Scheme 45, oxidation of 155 and 160 with both oxone (potassium peroxymonosulfate) and H2O2 afforded the one-ring-opened product 177. Interestingly, when these compounds

• -7,7,8,8-tetracyanoquinodimethane (F4-TCNQ). On the other hand, when compounds 178 and 179 were reacted with oxidizing agents such as oxone and H2O2, selectively one benzene ring-cleaved products 180 and 181 were isolated (Scheme 46) [85]. Having the ring-opened products in hands, they were then subjected

One-pot synthesis of isosorbide from cellulose or lignocellulosic biomass: a challenge?

• Isaline Bonnin,
• Raphaël Mereau,
• Thierry Tassaing and
• Karine De Oliveira Vigier

Beilstein J. Org. Chem. 2020, 16, 1713–1721, doi:10.3762/bjoc.16.143

• 1.5 h in an ethanol/water (50:50) mixture at 210 °C, and ii) CIMV (Compagnie Industrielle de la Matière Végétale) technology, where wheat straw was treated during 3.5 h of acetic acid/formic acid/water (50:30:15 m/m/m) extraction at 105 °C and then in the presence of H2O2 and organic acids (peracetic

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

• used for the photocatalytic generation of H2O2, the degradation of methylene blue dye, and the reduction of nitrobenzene to aniline. Although it was an interesting and novel approach to efficiently irradiating HPCats, the report did not address the potential concerns with the heat dissipation from the

4-Hydroxy-3-methyl-2(1H)-quinolone, originally discovered from a Brassicaceae plant, produced by a soil bacterium of the genus Burkholderia sp.: determination of a preferred tautomer and antioxidant activity

• Dandan Li,
• Naoya Oku,
• Yukiko Shinozaki,
• Yoichi Kurokawa and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2020, 16, 1489–1494, doi:10.3762/bjoc.16.124

• caused biphasic separation of the mixture. Antimicrobial assay The antimicrobial activity was evaluated by the method described previously [16]. Antioxidant assay The antioxidant activity was evaluated by the method described in [41]. Briefly, luminol (10 μM), H2O2 (1000 μM), and vehicle solvent with or

Synthesis of 3-substituted isoxazolidin-4-ols using hydroboration–oxidation reactions of 4,5-unsubstituted 2,3-dihydroisoxazoles

• Lívia Dikošová,
• Júlia Laceková,
• Ondrej Záborský and
• Róbert Fischer

Beilstein J. Org. Chem. 2020, 16, 1313–1319, doi:10.3762/bjoc.16.112

• oxidation step, after the disappearance of the starting material, 10% aqueous NaOH and 35% aqueous H2O2 were added at 0 °C dropwise as slowly as possible. It turned out that a patient addition of both NaOH (aq) and H2O2 (aq) accompanied by intense cooling is a crucial part of the procedure, preventing the

• -substituted isoxazolidin-4-ols employing the hydroboration–oxidation reaction of 4,5-unsubstituted 2,3-dihydroisoxazoles with basic hydrogen peroxide. A patient addition of both NaOH (aq) and H2O2 (aq) accompanied by intense cooling was a crucial part of the procedure in terms of product yield. All

• ), a 10% solution of NaOH (7.5 mL) was added dropwise as slowly as possible at 0 °C, followed by a 35% solution of H2O2 (15 mL) added in a likewise manner. After 3 h of stirring at 0 °C (TLC, hexanes/EtOAc, 1:1), the reaction was diluted with EtOAc (30 mL). The organic layer was separated, washed with

Oxime radicals: generation, properties and application in organic synthesis

• Igor B. Krylov,
• Stanislav A. Paveliev,
• Alexander S. Budnikov and
• Alexander O. Terent’ev

Beilstein J. Org. Chem. 2020, 16, 1234–1276, doi:10.3762/bjoc.16.107

• [46], Pb(OAc)4 [44][46][47][48][49][50][51], PbO2 [52], Mn(OAc)3 [46], KMnO4 [46], Ag2O [53], AgO [54], Horseradish peroxidase/H2O2 [55], metal-free oxidants PhI(OAc)2 [46], t-BuOOt-Bu [53] or quinones [56] under UV irradiation. Anodic oxidation was also reported [57]. The establishing of the self

Activated carbon as catalyst support: precursors, preparation, modification and characterization

• Melanie Iwanow,
• Tobias Gärtner,
• Volker Sieber and
• Burkhard König

Beilstein J. Org. Chem. 2020, 16, 1188–1202, doi:10.3762/bjoc.16.104

• of oxygen-containing surface groups can be influenced by treatment with different oxidants such as H2O2, HNO3, oxygen/ air, ozone or NaOCl. Thereby, the acidic or basic behavior and the resulting surface chemistry of the activated carbons are determined. Jaramillo et al. investigated the influence of

• different oxidizing reagents on the activated carbon materials prepared from cherry stones. Different amounts of oxygen functional groups were found on the surface of the materials depending on the oxidizing agents used: HNO3 > O3 > H2O2 > O2 (air). Mostly carboxyl groups were formed by the oxidative

• similar porosity, but different amounts of oxygen groups on the surface. They observed a decrease of the hydrophobicity of the carbon surface due to formation of acidic groups by oxidization with H2O2. This property change based on the increase of oxygen surface groups made the surface more accessible for

Copper catalysis with redox-active ligands

• Agnideep Das,
• Yufeng Ren,
• Cheriehan Hessin and
• Marine Desage-El Murr

Beilstein J. Org. Chem. 2020, 16, 858–870, doi:10.3762/bjoc.16.77

• 6D, in which the H-atom is transferred from the secondary benzylic sp3 carbon to the redox-active ligand, acting as a cooperative H-atom acceptor. Following a proton-coupled electron transfer (PCET) to generate 6E, the oxidized product (benzaldehyde) is released and final elimination of H2O2

A systematic review on silica-, carbon-, and magnetic materials-supported copper species as efficient heterogeneous nanocatalysts in “click” reactions

• Pezhman Shiri and
• Jasem Aboonajmi

Beilstein J. Org. Chem. 2020, 16, 551–586, doi:10.3762/bjoc.16.52

• for 2 h. The mixture was also diluted with hot water and then, H2O2 was added to adjust the pH value and to terminate the reaction. In the next step, the resulting mixture was washed with distilled water, and the pure graphene oxide powder was gathered by centrifugation and dried. The GO was dispersed

A review of asymmetric synthetic organic electrochemistry and electrocatalysis: concepts, applications, recent developments and future directions

• Munmun Ghosh,
• Valmik S. Shinde and
• Magnus Rueping

Beilstein J. Org. Chem. 2019, 15, 2710–2746, doi:10.3762/bjoc.15.264

• chloroperoxidase catalyst. H2O2 generated in situ from the cathodic reduction of oxygen was proposed to be responsible for the enzyme-mediated thiol ether oxidation (Scheme 47) [82]. Vitamin B12-dependent enzymes are an exciting representative in the family of chiral inductors for electroorganic chemistry. These

Chiral terpene auxiliaries V: Synthesis of new chiral γ-hydroxyphosphine oxides derived from α-pinene

• Anna Kmieciak and
• Marek P. Krzemiński

Beilstein J. Org. Chem. 2019, 15, 2493–2499, doi:10.3762/bjoc.15.242

• (H2O2/NaOH) proceeded with the low yield (32%). Application of m-chloroperbenzoic acid (mCPBA) as an oxidant, similarly to Knochels findings [19], gave the higher yield (56%) of (((1R,2R,3R,4R,5R)-4-hydroxypinan-3-yl)methyl)diphenylphosphine oxide (22). Next, phosphine oxide 22 was reduced to the

Synthesis of 1-azaspiro[4.4]nonan-1-oxyls via intramolecular 1,3-dipolar cycloaddition

• Yulia V. Khoroshunova,
• Denis A. Morozov,
• Andrey I. Taratayko,
• Polina D. Gladkikh,
• Yuri I. Glazachev and
• Igor A. Kirilyuk

Beilstein J. Org. Chem. 2019, 15, 2036–2042, doi:10.3762/bjoc.15.200

• performed for reductive isoxazolidine ring opening [15][16] producing aminoalcohols 9a–c in 85–95% yields (Scheme 2). We have previously reported that oxidation of secondary amines with a spiro(2-hydroxymethyl)cyclopentane moiety at the α-carbon with the H2O2/WO42− system is ineffective whereas conversion

A review of the total syntheses of triptolide

• Xiang Zhang,
• Zaozao Xiao and
• Hongtao Xu

Beilstein J. Org. Chem. 2019, 15, 1984–1995, doi:10.3762/bjoc.15.194

• the desired stereochemistry of the C-7 benzylic hydroxy group. Compound 46 was converted to triptonide 2 by Alder periodate reaction (NaIO4, 74%), and a sequencing m-CPBA epoxidation and basic hydrogen peroxide oxidation (H2O2/OH−) procedure (two steps, 28%). Finally, sodium borohydride reduction of 2

• epoxydienone via the methodology developed by Alder et al., which was treated without purification with basic H2O2 to yield diepoxide 67, along with its 12,13-β-isomer. The mixture was immediately oxidized with 3,5-(NO2)2C6H3CO3H and Na2HPO4 to give triptonide (2, 15% from 67), and reduction of triptonide via

Application of chiral 2-isoxazoline for the synthesis of syn-1,3-diol analogs

• Juanjuan Feng,
• Tianyu Li,
• Jiaxin Zhang and
• Peng Jiao

Beilstein J. Org. Chem. 2019, 15, 1840–1847, doi:10.3762/bjoc.15.179

• reduction [4][5][6][7][8][9][10][11] of 7 using Et2BOMe and NaBH4 at −78 °C gave stable ethylboronate 8 in 96% yield. Several ethylboronate compounds have been reported [9][10][11][56][57][58][59][60][61][62]. From 8 to 9, no H2O2 treatment was necessary. Rotary evaporation of 8 with CH3OH at ca. 40 °C

Metal-free mechanochemical oxidations in Ertalyte^® jars

• Andrea Porcheddu,
• Francesco Delogu,
• Lidia De Luca,
• Claudia Fattuoni and
• Evelina Colacino

Beilstein J. Org. Chem. 2019, 15, 1786–1794, doi:10.3762/bjoc.15.172

• process [55]. Also, Oxone® and NH2CONH2·H2O2 appeared to fail in the oxidation of 3-phenyl-1-propanol (1a) to the corresponding aldehyde. Subsequently, we turned our attention to sodium hypochlorite (NaOCl), an inexpensive and widely used oxidizing reagent also applied as a disinfectant and household

N-(1-Phenylethyl)aziridine-2-carboxylate esters in the synthesis of biologically relevant compounds

• Iwona E. Głowacka,
• Aleksandra Trocha,
• Andrzej E. Wróblewski and
• Dorota G. Piotrowska

Beilstein J. Org. Chem. 2019, 15, 1722–1757, doi:10.3762/bjoc.15.168

Stereo- and regioselective hydroboration of 1-exo-methylene pyranoses: discovery of aryltriazolylmethyl C-galactopyranosides as selective galectin-1 inhibitors

• Alexander Dahlqvist,
• Axel Furevi,
• Niklas Warlin,
• Hakon Leffler and
• Ulf J. Nilsson

Beilstein J. Org. Chem. 2019, 15, 1046–1060, doi:10.3762/bjoc.15.102

Easy, efficient and versatile one-pot synthesis of Janus-type-substituted fullerenols

• Marius Kunkel and
• Sebastian Polarz

Beilstein J. Org. Chem. 2019, 15, 901–905, doi:10.3762/bjoc.15.87

• tetrabutylammonium hydroxide (0.5 mL of a 30% solution in H2O). The reactants for the polyhydroxylation are added, H2O2 (1.5 mL of a 30% solution) and NaOH (0.7 g). The mixture is heated to reflux until the chlorobenzene phase decolorizes. The reaction is completed after 2 h of reflux. The aqueous phase is separated

An efficient synthesis of the guaiane sesquiterpene (−)-isoguaiene by domino metathesis

• Yuzhou Wang,
• Ahmed F. Darweesh,
• Patrick Zimdars and
• Peter Metz

Beilstein J. Org. Chem. 2019, 15, 858–862, doi:10.3762/bjoc.15.83

• analysis for (−)-isoguaiene (1). Synthesis of 1 by relay metathesis of trienyne 3. a) HC(OMe)3, 4 mol % LiBF4, MeOH, reflux, 80%; b) (i) BH3·Me2S, THF, 0 °C to rt, (ii) 30% H2O2, 10% NaOH, 0 °C to rt, 97%; c) 5 mol % TPAP, NMO, CH2Cl2, rt, 97%; d) 13, THF, rt to reflux, 96%; e) 25 mol % TsOH, THF, H2O

An efficient and concise access to 2-amino-4H-benzothiopyran-4-one derivatives

• Peng Li,
• Yongqi Wu,
• Tingting Zhang,
• Chen Ma,
• Ziyun Lin,
• Gang Li and
• Haihong Huang

Beilstein J. Org. Chem. 2019, 15, 703–709, doi:10.3762/bjoc.15.65

• from 2’-chloroacetophenone as the starting material through treatment with carbon disulfide in the presence of sodium hydride [23], followed by alkylation using iodoethane according to the literature procedures [13][16][17][19]. The oxidation of 1 with 1.2 or 5 equiv of H2O2 yielded ethyl sulfoxide 2

Synthesis of nonracemic hydroxyglutamic acids

• Dorota G. Piotrowska,
• Iwona E. Głowacka,
• Andrzej E. Wróblewski and
• Liwia Lubowiecka

Beilstein J. Org. Chem. 2019, 15, 236–255, doi:10.3762/bjoc.15.22

• . Reagents and conditions: a) NaClO2, 30% H2O2, NaH2PO4, MeCN; b) ClCOOEt, NEt3, then CH2N2, ether; c) MeOH, PhCOOAg, NEt3; d) LiOH, THF/H2O; e) ClCOOBn, NEt3, DMAP; f) TFA, H2O; g) NaIO4, acetone/water; h) NaHCO3, THF/H2O; i) H2C=CHCH2Br, NaHCO3, DMF; j) H2, 10% Pd/C, MeOH/HCl. Synthesis of (4S)-4-hydroxy-L

• , ethanol/water. Synthesis of the orthogonally protected 4-hydroxyglutamic acid (2S,4S)-73. Reagents and conditions: a) toluene, 25 °C; b) LiOH, H2O2/THF; c) O-tert-butyl-N,N′-diisopropylisourea, CuCl; d) H2, 10% Pd/C, Boc2O, MeOH. Synthesis of (2S,4R)-4-acetyloxyglutamic acid as a component of a dipeptide

• protected serinal (R)-23. Reagents and conditions: a) Ph3P=CHCOOMe, benzene; b) Ac2O, NEt3, DMAP, CH2Cl2; c) 30% H2O2, PTSA, MgSO4, DME; d) K2CO3, MeOH; e) MeOH, 45 °C; f) Piv2O, NEt3, DMAP, CH2Cl2; g) PTSA, MeOH; h) CrO3, H5IO6, MeCN; i) 6 M HCl, reflux. Synthesis of (2S,3S,4S)-4 from O-benzyl-N-Boc-D

Unexpected loss of stereoselectivity in glycosylation reactions during the synthesis of chondroitin sulfate oligosaccharides

• Teresa Mena-Barragán,
• José L. de Paz and
• Pedro M. Nieto

Beilstein J. Org. Chem. 2019, 15, 137–144, doi:10.3762/bjoc.15.14

• assays, deprotection of dimer 6 and tetramer 14β were accomplished (Scheme 5). Compound 14α was also submitted to the deprotection sequence to obtain a non-natural α-containing oligosaccharide. Basic hydrolysis using H2O2/LiOH and then NaOH followed by selective N-acetylation in MeOH afforded CS

• , 25% (14α) + 33% (14β). Reagents and conditions: a) LiOH, H2O2, THF, −5 °C to rt, 24 h, then NaOH, MeOH, 72 h, then Ac2O, Et3N, MeOH, 2 h, 38% (15); 30% (16α); 73% (16β). Reagents and conditions: a) 2-propanol, TMSOTf, CH2Cl2, 0 °C, 30 min, 73%; b) NH2NH2·H2O, Py/AcOH, CH2Cl2, 1 h, 89%; c) 1, TMSOTf