Repurposing the anticancer drug cisplatin with the aim of developing novel Pseudomonas aeruginosa infection control agents

• Mingjun Yuan,
• Song Lin Chua,
• Yang Liu,
• Daniela I. Drautz-Moses,
• Joey Kuok Hoong Yam,
• Thet Tun Aung,
• Roger W. Beuerman,
• May Margarette Santillan Salido,
• Stephan C. Schuster,
• Choon-Hong Tan,
• Michael Givskov,
• Liang Yang and
• Thomas E. Nielsen

Beilstein J. Org. Chem. 2018, 14, 3059–3069, doi:10.3762/bjoc.14.284

• ] and hydrogen peroxide treatments [32]. In addition, cisplatin treatment induced the expression of a series of genes involved in energy metabolism, which corroborated with previous proteomics work showing that cisplatin could interfere with stress response and energy metabolism in E. coli [33]. To

Degenerative xanthate transfer to olefins under visible-light photocatalysis

• Atsushi Kaga,
• Xiangyang Wu,
• Joel Yi Jie Lim,
• Hirohito Hayashi,
• Yunpeng Lu,
• Edwin K. L. Yeow and
• Shunsuke Chiba

Beilstein J. Org. Chem. 2018, 14, 3047–3058, doi:10.3762/bjoc.14.283

• (Scheme 1A). Peroxide initiators such as dilauroyl peroxide (DLP) are commonly utilized [1][2][3][4][5][6][7][8][9][10][11][12][13][14], while decomposition of DLP needs a high reaction temperature and inevitably generates considerable amounts of byproducts derived from DLP that sometimes require tedious

Copper(I)-catalyzed tandem reaction: synthesis of 1,4-disubstituted 1,2,3-triazoles from alkyl diacyl peroxides, azidotrimethylsilane, and alkynes

• Muhammad Israr,
• Changqing Ye,
• Munira Taj Muhammad,
• Yajun Li and
• Hongli Bao

Beilstein J. Org. Chem. 2018, 14, 2916–2922, doi:10.3762/bjoc.14.270

• found that alkyl azide has always appeared as a side product when the reaction involved TMSN3 and alkyl diacyl peroxide, easily available compounds derived from aliphatic carboxylic acids. With this information in mind, initially, we started our investigation with phenylacetylene (1a), commercially

• available lauroyl peroxide (2a), and TMSN3 (Table 1). In a preliminary experiment, the reaction of 1a with 2a in the presence of 10 mol % of CuCl in THF at 50 °C afforded 1,4-disubstituted 1,2,3-triazole 3a in 65% isolated yield (Table 1, entry 1). Surprisingly, under these conditions no CuAAC product

• . Furthermore, the scope of the alkyl diacyl peroxides was then studied (Scheme 3). The alkyl diacyl peroxides 2 were synthesized from the corresponding aliphatic carboxylic acids in a single step by DCC-mediated dehydrative condensation with hydrogen peroxide, and were used directly after simple filtration

An overview on recent advances in the synthesis of sulfonated organic materials, sulfonated silica materials, and sulfonated carbon materials and their catalytic applications in chemical processes

• Hashem Sharghi,
• Pezhman Shiri and
• Mahdi Aberi

Beilstein J. Org. Chem. 2018, 14, 2745–2770, doi:10.3762/bjoc.14.253

• permanganate was added and stirred at 35 °C for 2 h. In the next step, the reaction mixture was cooled to 0 °C. Hydrogen peroxide (30%) in deionized water was added to the reaction mixture. The solid was gathered by centrifugation, washed with deionized water, methanol, and ether, and then dried at 40 °C under

Bioinspired cobalt cubanes with tunable redox potentials for photocatalytic water oxidation and CO₂ reduction

• Zhishan Luo,
• Yidong Hou,
• Jinshui Zhang,
• Sibo Wang and
• Xinchen Wang

Beilstein J. Org. Chem. 2018, 14, 2331–2339, doi:10.3762/bjoc.14.208

• g, 10 mmol) and CH3CO2Na·3H2O (2.7 g, 20 mmol) in methanol (30 mL) heated to refluxing temperature, is added pyridine (0.8 mL, 10 mmol) while stirring. Then a portion of 30% hydrogen peroxide (v/v, 5 mL, 50 mmol) is slowly added to the reaction mixture, and stirring under refluxing conditions is

The enzymes of microbial nicotine metabolism

• Paul F. Fitzpatrick

Beilstein J. Org. Chem. 2018, 14, 2295–2307, doi:10.3762/bjoc.14.204

• it contains covalently-bound FAD and produces hydrogen peroxide as a product in addition to 4-aminobutryate [5][38]. Mabo also catalyzes the oxidative demethylation of sarcosine. Based on these results, the mechanism of the enzyme is similar to that of sarcosine oxidase, direct oxidation of the C–N

Hypervalent iodine compounds for anti-Markovnikov-type iodo-oxyimidation of vinylarenes

• Igor B. Krylov,
• Stanislav A. Paveliev,
• Mikhail A. Syroeshkin,
• Alexander A. Korlyukov,
• Pavel V. Dorovatovskii,
• Yan V. Zubavichus,
• Gennady I. Nikishin and
• Alexander O. Terent’ev

Beilstein J. Org. Chem. 2018, 14, 2146–2155, doi:10.3762/bjoc.14.188

• %) was obtained using PhI(OAc)2 (Table 1, entry 2). Other iodine-based oxidants, such as PhI(OCOCF3)2 (Table 1, entry 10, yield 31%), IBX (Table 1, entries 11 and 12, yield 32–54%), DMP (Table 1, entries 13–14, yield 52%), showed less efficacy in this process. Peroxide oxidants, such as TBHP, TBAI/TBHP

A pyridinium/anilinium [2]catenane that operates as an acid–base driven optical switch

• Sarah J. Vella and
• Stephen J. Loeb

Beilstein J. Org. Chem. 2018, 14, 1908–1916, doi:10.3762/bjoc.14.165

• peroxide was purchased from Acros and used as received. Compounds 3 [18], [5][OTf]2 [19][20] and 6 [21] were prepared using literature methods. Solvents were dried using an Innovative Technologies solvent purification system. Thin-layer chromatography (TLC) was performed using Teledyne Silica gel 60 F254

Recent advances in hypervalent iodine(III)-catalyzed functionalization of alkenes

• Xiang Li,
• Pinhong Chen and
• Guosheng Liu

Beilstein J. Org. Chem. 2018, 14, 1813–1825, doi:10.3762/bjoc.14.154

• was used as a stoichiometric oxidant [45]. In contrast to the intramolecular cyclization, the intermolecular reaction is much more attractive. Li and co-workers reported a syn-diacetoxylation of alkenes, using iodoarenes as catalyst which was oxidized to hypervalent iodine(III) by hydrogen peroxide in

An amine protecting group deprotectable under nearly neutral oxidative conditions

• Shahien Shahsavari,
• Chase McNamara,
• Mark Sylvester,
• Emily Bromley,
• Savannah Joslin,
• Bao-Yuan Lu and
• Shiyue Fang

Beilstein J. Org. Chem. 2018, 14, 1750–1757, doi:10.3762/bjoc.14.149

• conditions [13][14][15][16][17]. This group was deprotected under oxidative conditions under which the commonly used Boc, Fmoc, benzyl and Teoc groups could potentially survive. Oxidation was achieved by hydrogen peroxide in the presence of an ammonium molybdate catalyst. Recently, we reported the use of the

β-Hydroxy sulfides and their syntheses

• Mokgethwa B. Marakalala,
• Edwin M. Mmutlane and
• Henok H. Kinfe

Beilstein J. Org. Chem. 2018, 14, 1668–1692, doi:10.3762/bjoc.14.143

• . Carrying out the one-pot thiolysis then oxidation with hydrogen peroxide proceeded uneventfully to give the corresponding β-hydroxy sulfoxides 35 and 36 in good to excellent yields (Scheme 7). Moreover, the reaction was found to be compatible with the less nucleophilic thiols such as p-fluorothiophenol and

• from the thiophenol to form β-peroxysulfide 84. Cleavage of the O–O bond of the peroxide followed by protonation liberates the desired β-hydroxy sulfide 81. This methodology is quite general considering the number of substituents used in both the styrenes and thiophenols. 3.2.4 Rongalite catalysis

A survey of chiral hypervalent iodine reagents in asymmetric synthesis

• Soumen Ghosh,
• Suman Pradhan and
• Indranil Chatterjee

Beilstein J. Org. Chem. 2018, 14, 1244–1262, doi:10.3762/bjoc.14.107

• -symmetric I(III) reagent 8b was used to obtain high enantioselectivity. Ishihara et al. appealingly reported an oxidative cycloetherification of ketophenols 92 in the presence of an in situ generated chiral quaternary ammonium (hypo)iodite salt 94, with hydrogen peroxide as an oxidant to deliver chiral

One hundred years of benzotropone chemistry

• Arif Dastan,
• Haydar Kilic and
• Nurullah Saracoglu

Beilstein J. Org. Chem. 2018, 14, 1120–1180, doi:10.3762/bjoc.14.98

• method for the synthesis of 2,3-benzotropone (12) starting with 1-benzosuberone (162) (Scheme 29) [134]. First, the unsaturated ketone 163, which is called Julia’s ketone, was prepared by NBS-bromination in the presence of a trace of benzoyl peroxide (BPO) and followed by dehydrobromination. Another

• structures for both pairs (271 or 272) are not clear. However, the oxidation of both 239 and 264 to o-carboxycinnamic acid (273) was also reported under alkaline hydrogen peroxide conditions (Scheme 42) [163][164]. Furthermore, bromination of 6-hydroxy-2,3-benzotropone (239) and corresponding transformations

• synthesis of 7-hydroxy-2,3-benzotropone (241) was successfully realized by Dastan’s group (Scheme 47) [149]. Thiourea reduction of the peroxide linkage of 213 to the diol 282 and then simultaneously dehydration in situ gave the corresponding benzotropolone 241 in nearly quantitative yield. Recently, Arican

Selective carboxylation of reactive benzylic C–H bonds by a hypervalent iodine(III)/inorganic bromide oxidation system

• Toshifumi Dohi,
• Shohei Ueda,
• Kosuke Iwasaki,
• Yusuke Tsunoda,
• Koji Morimoto and
• Yasuyuki Kita

Beilstein J. Org. Chem. 2018, 14, 1087–1094, doi:10.3762/bjoc.14.94

• benzylmethyl groups, and the use of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) [58] or catalytic tetrabutylammonium iodide with tert-butyl hydrogen peroxide for reactions with a large excess of aromatic hydrocarbons [59]. Other than these excellent examples of metal-free methods, two protocols using a

An overview of recent advances in duplex DNA recognition by small molecules

• Sayantan Bhaduri,
• Nihar Ranjan and
• Dev P. Arya

Beilstein J. Org. Chem. 2018, 14, 1051–1086, doi:10.3762/bjoc.14.93

• groove binders, whereas the third complex prefers an intercalative mode of binding to DNA. All these complexes show nuclease activity in the presence of hydrogen peroxide and induce apoptosis to human A549 lung adenocarcinoma cells. A series of novel glyco-oligoamides (Figure 9) has been designed and

An uracil-linked hydroxyflavone probe for the recognition of ATP

• Márton Bojtár,
• Péter Zoltán Janzsó-Berend,
• Dávid Mester,
• Dóra Hessz,
• Mihály Kállay,
• Miklós Kubinyi and
• István Bitter

Beilstein J. Org. Chem. 2018, 14, 747–755, doi:10.3762/bjoc.14.63

• alkaline hydrogen peroxide to obtain the clickable fluorophore. All new compounds were characterized by NMR and high-resolution mass spectrometry. Optical spectroscopy The solubility of the UHF probe was very poor in water which resulted in the decrease of fluorescence over time upon dilution from the

• -hydroxy-7-propargyloxy-4H-chromen-4-one (3): Chalcone 2 (500 mg, 1.56 mmol) was dissolved in ethanol (25 mL) and sodium hydroxide (700 mg, 17.6 mmol, 11 equiv), dissolved in water (12.5 mL), was added. To the deep red solution was added 0.75 mL 30% hydrogen peroxide and the mixture was stirred at room

• analytes were added in 0.3 mM concentration. Ratio of the fluorescence intensities at 540 nm, the samples were excited at 470 and 400 nm. The red curve represents the result of a non-linear fitting. Synthesis of UHF. (i) 4-Dimethylaminobenzaldehyde, DMF, NaOMe, rt, 17 h, (ii) hydrogen peroxide, NaOH

Nanoreactors for green catalysis

• M. Teresa De Martino,
• Loai K. E. A. Abdelmohsen,
• Floris P. J. T. Rutjes and
• Jan C. M. van Hest

Beilstein J. Org. Chem. 2018, 14, 716–733, doi:10.3762/bjoc.14.61

• of glucose oxidase (GOx) to convert glucose into D-glucono-δ-lactone and hydrogen peroxide was the first step of the reaction (Scheme 3A); subsequently, myoglobin (Myo) employed the hydrogen peroxide produced to oxidize guaiacol to quinone and water (Scheme 3B). When the pH was below 7, the

Cobalt-catalyzed directed C–H alkenylation of pivalophenone N–H imine with alkenyl phosphates

• Wengang Xu and
• Naohiko Yoshikai

Beilstein J. Org. Chem. 2018, 14, 709–715, doi:10.3762/bjoc.14.60

• alkenylation reaction, affording the product 3aj with an E/Z ratio of 4:1. In our previous study on the C–H alkylation and arylation of pivalophenone N–H imines, we demonstrated that the pivaloyl imine readily undergoes fragmentation into a cyano group via an iminyl radical under peroxide photolysis or copper

• -catalyzed aerobic conditions [29]. Under the same peroxide photolysis conditions (t-BuOOt-Bu with UV (254 nm) irradiation), the ortho-alkenylated imine 3aa underwent a C–N bond-forming cyclization to afford the spirocyclic imine 4 in 81% yield (Scheme 4). The reaction likely involves the initial formation

Biocatalytic synthesis of the Green Note trans-2-hexenal in a continuous-flow microreactor

• Morten M. C. H. van Schie,
• Tiago Pedroso de Almeida,
• Gabriele Laudadio,
• Florian Tieves,
• Elena Fernández-Fueyo,
• Timothy Noël,
• Isabel W. C. E. Arends and
• Frank Hollmann

Beilstein J. Org. Chem. 2018, 14, 697–703, doi:10.3762/bjoc.14.58

• spectrophotometer, following the oxidation of ABTS (ε405 = 36,800 M−1 cm−1) by horseradish peroxidase (POD) at the expense of hydrogen peroxide. In general, 0.044 µM PeAAOx was used to convert 3 mM of trans-2-hex-2-enol. The hydrogen peroxide formed in this reaction was subsequently used to convert 2 mM of ABTS to

Functionalization of N-arylglycine esters: electrocatalytic access to C–C bonds mediated by n-Bu₄NI

• Mi-Hai Luo,
• Yang-Ye Jiang,
• Kun Xu,
• Yong-Guo Liu,
• Bao-Guo Sun and
• Cheng-Chu Zeng

Beilstein J. Org. Chem. 2018, 14, 499–505, doi:10.3762/bjoc.14.35

• terminal oxidants [14]. The protocol was also extended to reactions with 2-alkylquinoline [15] and phenols [16] using O2 and di-tert-butyl peroxide (DTBP) as oxidant, respectively (Scheme 1). A CuCl-catalyzed oxidative cross coupling of glycine derivatives with indoles has been developed by Hou et al

Preparation of trinucleotide phosphoramidites as synthons for the synthesis of gene libraries

• Ruth Suchsland,
• Bettina Appel and
• Sabine Müller

Beilstein J. Org. Chem. 2018, 14, 397–406, doi:10.3762/bjoc.14.28

• solvents and to precipitate upon the addition of a polar solvent, typically methanol. After coupling of a standard phosphoramidite building block followed by oxidation with 2-butanone peroxide in dichloromethane, the resulting dimer on the support was again precipitated with methanol and filtered, before

One-pot preparation of 4-aryl-3-bromocoumarins from 4-aryl-2-propynoic acids with diaryliodonium salts, TBAB, and Na₂S₂O₈

• Teppei Sasaki,
• Katsuhiko Moriyama and
• Hideo Togo

Beilstein J. Org. Chem. 2018, 14, 345–353, doi:10.3762/bjoc.14.22

• [27], with R-CH=O/(n-Bu)4NBr (TBAB, cat.)/K2S2O8 at 90 °C [28], with ArSO2H/Eosin Y(cat.)/tert-butyl hydrogen peroxide (TBHP) at rt [29], and with ArSO2NHNH2/n-Bu4NI(cat.)/TBHP at 80 °C [30]. In addition, the formation of coumarins via the bromine-radical-mediated reaction of aryl 2-alkynoates with

5-Aminopyrazole as precursor in design and synthesis of fused pyrazoloazines

• Ranjana Aggarwal and
• Suresh Kumar

Beilstein J. Org. Chem. 2018, 14, 203–242, doi:10.3762/bjoc.14.15

• pyrazolo[3,4-d]pyrimidine derivatives starting from 5-amino-4-cyanopyrazoles 208 (Scheme 57). 5-Amino-4-cyanopyrazole 208 was benzoylated with p-nitrobenzoyl chloride (209) and subsequently cyclized to pyrazolo[3,4-d]pyrimidine derivative 211 by refluxing in sodium hydroxide and hydrogen peroxide

Progress in copper-catalyzed trifluoromethylation

• Guan-bao Li,
• Chao Zhang,
• Chun Song and
• Yu-dao Ma

Beilstein J. Org. Chem. 2018, 14, 155–181, doi:10.3762/bjoc.14.11

• showed lower efficiency. Then, they extended the substrate scope to 1,3-azoles and perfluoroarenes. Di-tert-butyl peroxide was chosen as a suitable oxidant instead of air. Functional groups, such as chloro and bromo, were compatible in this reaction, providing a complementary platform for further

Photocatalytic formation of carbon–sulfur bonds

• Alexander Wimmer and
• Burkhard König

Beilstein J. Org. Chem. 2018, 14, 54–83, doi:10.3762/bjoc.14.4

• radical anion then deprotonates the thiyl radical cation. Subsequent addition to the alkene yields the anti-Markovnikov radical intermediate. Radical addition to dioxygen leads finally to the β-ketosulfide, which subsequently is oxidized by the in situ generated hydrogen peroxide radical to the respective

• β-ketosulfoxide. No additional sacrificial substrates are needed in order to regenerate the photocatalyst or for the oxidation of the sulfenyl intermediate to the respective sulfoxide moiety. Hydrogen peroxide, which is generated as a byproduct, directly is consumed by oxidizing the sulfide to the