Deep-blue emitting 9,10-bis(perfluorobenzyl)anthracene

• Long K. San,
• Sebastian Balser,
• Brian J. Reeves,
• Tyler T. Clikeman,
• Yu-Sheng Chen,
• Steven H. Strauss and
• Olga V. Boltalina

Beilstein J. Org. Chem. 2025, 21, 515–525, doi:10.3762/bjoc.21.39

• (trifluoromethyl)benzene (1,4-C6H4(CF3)2, Central Glass Co., 99%); dimethyl sulfoxide (DMSO, Fisher Scientific, ACS grade); anhydrous magnesium sulfate (MgSO4, Fisher Scientific); Cu powder (Strem Chemicals, 99%); dichloromethane (EMD Chemicals, ACS grade); acetone (technical grade); THF (Aldrich/Merck, ACS grade

Synthesis, characterization, antimicrobial, cytotoxic and carbonic anhydrase inhibition activities of multifunctional pyrazolo-1,2-benzothiazine acetamides

• Ayesha Saeed,
• Shahana Ehsan,
• Muhammad Zia-ur-Rehman,
• Erin M. Marshall,
• Sandra Loesgen,
• Abdus Saleem,
• Simone Giovannuzzi and
• Claudiu T. Supuran

Beilstein J. Org. Chem. 2025, 21, 348–357, doi:10.3762/bjoc.21.25

• microbroth single-dose assays. Dimethyl sulfoxide was used at a final concentration of 0.1% as negative control. Microbroth dilution assays [52] for the most potent bioactive compounds 7b and 7h were performed using nine serial dilutions of the tested compounds with final concentrations of 256, 128, 64, 32

Direct trifluoroethylation of carbonyl sulfoxonium ylides using hypervalent iodine compounds

• Radell Echemendía,
• Carlee A. Montgomery,
• Fabio Cuzzucoli,
• Antonio C. B. Burtoloso and
• Graham K. Murphy

Beilstein J. Org. Chem. 2024, 20, 3182–3190, doi:10.3762/bjoc.20.263

• those that lead to α-alkyl-substituted compounds, is still challenging [27]. For example, in the SN2 reaction of alkyl halides with sulfoxonium ylides, the initially formed α-alkyl-substituted ylide reacts further with the halide to expel the sulfoxide and ultimately generate an α-halogenated product

Cyclodextrin-based rotaxanes for polymer materials: challenge on simultaneous realization of inexpensive production and defined structures

• Yosuke Akae

Beilstein J. Org. Chem. 2024, 20, 3026–3049, doi:10.3762/bjoc.20.252

• sulfoxide (DMSO) must be available as CD forms the inclusion complex), (5) the yield of the end-capping reaction must be high, (6) the end-capping reagent and rotaxane must dissolve in the same solvent to facilitate a homogeneous reaction, and (7) the rotaxane must be isolable from the reaction mixture. The

Recent advances in transition-metal-free arylation reactions involving hypervalent iodine salts

• Ritu Mamgain,
• Kokila Sakthivel and
• Fateh V. Singh

Beilstein J. Org. Chem. 2024, 20, 2891–2920, doi:10.3762/bjoc.20.243

Interaction of a pyrene derivative with cationic [60]fullerene in phospholipid membranes and its effects on photodynamic actions

• Hayato Takagi,
• Çetin Çelik,
• Ryosuke Fukuda,
• Qi Guo,
• Tomohiro Higashino,
• Hiroshi Imahori,
• Yoko Yamakoshi and
• Tatsuya Murakami

Beilstein J. Org. Chem. 2024, 20, 2732–2738, doi:10.3762/bjoc.20.231

• inability of O2•– detection is not known at present. Upon addition of dimethyl sulfoxide (DMSO) to this system, an adduct of DEPMPO and •CH3 (DEPMPO-CH3), which was presumably generated from the reaction of •OH and DMSO, was clearly observed, further confirming the generation of •OH (Figure 5b(iii)). At the

• by blue LED lamp. (iii) catC60 5 µM, NADH 8 mM, DETAPAC 1 mM, and DEPMPO 100 mM in a 4-to-1 (v/v) mixture of PBS(–) and dimethyl sulfoxide (DMSO) under irradiation for 30 min by blue LED lamp. (iv) catC60 5 µM, PyBA 67 µM, NADH 8 mM, DETAPAC 1 mM, and DEPMPO 100 mM in a 4-to-1 (v/v) mixture of PBS

A review of recent advances in electrochemical and photoelectrochemical late-stage functionalization classified by anodic oxidation, cathodic reduction, and paired electrolysis

• Nian Li,
• Ruzal Sitdikov,
• Ajit Prabhakar Kale,
• Joost Steverlynck,
• Bo Li and
• Magnus Rueping

Beilstein J. Org. Chem. 2024, 20, 2500–2566, doi:10.3762/bjoc.20.214

• anode to form a sulfoxide. Subsequent hydrogen atom abstraction by a chlorine radical leads to the formation of an intermediate carbon radical, whose resonant intermediate reacts with another chlorine radical to produce the desired α-chlorosulfoxide product (Scheme 14). 1.1.2 Unsaturated bond

HFIP as a versatile solvent in resorcin[n]arene synthesis

• Hormoz Khosravi,
• Valeria Stevens and
• Raúl Hernández Sánchez

Beilstein J. Org. Chem. 2024, 20, 2469–2475, doi:10.3762/bjoc.20.211

• , chlorinated species 1h and 1i, and carboxylic acid-containing 1s, developed high quality crystals from standing solutions in dimethyl sulfoxide for 1h and 1i, and methanol for 1s. Their molecular crystal structures were determined and are shown in Figure 1b displaying the classic cone conformation for both

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

• -azido-1-propanamine to give the desired AzidoTMT linker. Furthermore, Makarov et al. developed a linker containing a sulfoxide (SOX) group, which is well-known for specific fragmentation releasing the reporter ion at m/z 179.0849 (Figure 7C) [81][86][87]. The preparation of the tag is based on a five

gem-Difluorination of carbon–carbon triple bonds using Brønsted acid/Bu₄NBF₄ or electrogenerated acid

• Mizuki Yamaguchi,
• Hiroki Shimao,
• Kengo Hamasaki,
• Keiji Nishiwaki,
• Shigenori Kashimura and
• Kouichi Matsumoto

Beilstein J. Org. Chem. 2024, 20, 2261–2269, doi:10.3762/bjoc.20.194

• , entry 6), but TfOH gave the product 2a in 72% yield (Table 1, entry 7). As for the solvent, CH3CN slightly afforded 2a, although N,N-dimethylformamide (DMF) and dimethyl sulfoxide (DMSO) were not suitable for the reactions (Table 1, entries 8–10). A fluorine source, such as Bu4NF or BF3·Et2O, instead of

Cell-free protein synthesis with technical additives – expanding the parameter space of in vitro gene expression

• Tabea Bartsch,
• Stephan Lütz and
• Katrin Rosenthal

Beilstein J. Org. Chem. 2024, 20, 2242–2253, doi:10.3762/bjoc.20.192

• dimethyl sulfoxide (DMSO), methanol (MeOH), methyl tert-butyl ether (MTBE), and n-hexane. Measurements in triplicates. 0.5–1% only for MC and CMC. PEG, MC, CMC: % % w/v. Other: % % v/v. Note: 2% PEG-8000 is present as a standard component in all reactions, unless otherwise stated. n.d.: not determined

• ), methylcellulose (MC), carboxymethylcellulose (CMC), choline chloride/urea (ChCl/urea), choline chloride/glycerol (ChCl/glycerol), and betaine/ethylene glycol (betaine/EG). The reference experiment is labeled as shaded bars. B) represents dimethyl sulfoxide (DMSO), methanol (MeOH), methyl tert-butyl ether (MTBE

From perfluoroalkyl aryl sulfoxides to ortho thioethers

• Yang Li,
• Guillaume Dagousset,
• Emmanuel Magnier and
• Bruce Pégot

Beilstein J. Org. Chem. 2024, 20, 2108–2113, doi:10.3762/bjoc.20.181

• -pot two-step protocol. Several aryl-SCF3 compounds are reported by variation of the nitrile or of the trifluoroalkyl sulfoxide starting material. The variation of the perfluoroalkyl chain was also possible. Keywords: ortho functionalization; rearrangement; sulfoxide; Introduction Since decades

• Discussion We started our optimization with the reaction between acetonitrile and phenyl trifluoromethyl sulfoxide (1a, Table 1). We firstly chose the same stoichiometry as described in our previous study and tried to reduce the reaction time by the help of microwave heating (Table 1, entry 1). Under these

• decided to use 2 equivalents of DIPEA at low temperature. After ten minutes at −15 °C to allow for the reaction between phenyl trifluoromethyl sulfoxide (1a) and acetonitrile, the base was added and the reaction was stirred for the same amount of time. To our delight, a good NMR yield of 74% was received

Syntheses and medicinal chemistry of spiro heterocyclic steroids

• Laura L. Romero-Hernández,
• Ana Isabel Ahuja-Casarín,
• Penélope Merino-Montiel,
• Sara Montiel-Smith,
• José Luis Vega-Báez and
• Jesús Sandoval-Ramírez

Beilstein J. Org. Chem. 2024, 20, 1713–1745, doi:10.3762/bjoc.20.152

• through a one-pot multicomponent reaction (MCR) involving the reaction of substituted 2-aminopyridines, isocyanides, and the cholestanone derivatives 56 [36]. The reactions were conducted in dimethyl sulfoxide at 70 °C, and catalysed by propylphosphonic anhydride (T3P®), providing high yields in all cases

pKalculator: A pK_a predictor for C–H bonds

• Rasmus M. Borup,
• Nicolai Ree and
• Jan H. Jensen

Beilstein J. Org. Chem. 2024, 20, 1614–1622, doi:10.3762/bjoc.20.144

• complex molecules by exchanging a C–H bond with different functional groups to modify the biological activity of drugs [2]. However, pinpointing which C–H bond is reacting can be challenging. Grzybowski and co-workers recently addressed this gap by predicting pKa values for C–H bonds in dimethyl sulfoxide

• sulfoxide (DMSO, ε = 47.2) using GFN-FF-xTB [18] and the analytical linearized Poisson–Boltzmann (ALPB) equation [19] as the implicit solvation model. We then remove conformers with relative energies above 3 kcal/mol and select unique conformers by taking the centroids of a Butina clustering using pairwise

Generation of alkyl and acyl radicals by visible-light photoredox catalysis: direct activation of C–O bonds in organic transformations

• Mithu Roy,
• Bitan Sardar,
• Itu Mallick and
• Dipankar Srimani

Beilstein J. Org. Chem. 2024, 20, 1348–1375, doi:10.3762/bjoc.20.119

• salicylic acid derivatives and aryl acetylenes. Due to irradiation with blue light, Mes–Acr–Me+ gets excited to Mes–Acr–Me+* and takes up a single electron from Ph2S. The reaction of the diphenyl sulfide radical cation with carboxylate and successive acyloxy C–O bond cleavage forms diphenyl sulfoxide and an

Sustainable tandem acylation/Diels–Alder reaction toward versatile tricyclic epoxyisoindole-7-carboxylic acids in renewable green solvents

• Ayhan Yıldırım

Beilstein J. Org. Chem. 2024, 20, 1308–1319, doi:10.3762/bjoc.20.114

• chloroform-d (CDCl3) or hexadeuterodimethyl sulfoxide (DMSO-d6) as a solvent. Chemical shifts (δ) are reported in ppm and J values in Hertz. The elemental analyses were performed using an LECO CHNS-932 elemental analyzer (Saint Joseph, MI, USA). Representative procedure for the IMDAF reaction to afford 2a In

Structure–property relationships in dicyanopyrazinoquinoxalines and their hydrogen-bonding-capable dihydropyrazinoquinoxalinedione derivatives

• Tural N. Akhmedov,
• Ajeet Kumar,
• Daken J. Starkenburg,
• Kyle J. Chesney,
• Khalil A. Abboud,
• Novruz G. Akhmedov,
• Jiangeng Xue and
• Ronald K. Castellano

Beilstein J. Org. Chem. 2024, 20, 1037–1052, doi:10.3762/bjoc.20.92

• and its high thermal stability. Optical properties The electronic properties of the DCPQs 1a–6a and DPQDs 1b–7b were explored by UV–vis absorption spectroscopy in dimethyl sulfoxide (DMSO) at 25 °C (Figure 3). The electronic absorption spectra of DCPQs exhibited structureless bands with λmax values

• μM) for a) DCPQs 1a–6a and b) DPQDs 1b–7b in dimethyl sulfoxide. Calculated HOMO (below) and LUMO (above) energies by DFT analysis (B3LYP/6-31+G* level of theory), and corresponding molecular orbital plots for 1a–7a. Calculated HOMO (below) and LUMO (above) energies by DFT analysis (B3LYP/6-31+G

Auxiliary strategy for the general and practical synthesis of diaryliodonium(III) salts with diverse organocarboxylate counterions

• Naoki Miyamoto,
• Daichi Koseki,
• Kohei Sumida,
• Elghareeb E. Elboray,
• Naoko Takenaga,
• Ravi Kumar and
• Toshifumi Dohi

Beilstein J. Org. Chem. 2024, 20, 1020–1028, doi:10.3762/bjoc.20.90

• productivity in arylation processes [45]. These aryl(TMP)iodonium(III) carboxylates are stable at room temperature and are available as amorphous solids that dissolve in specific solvents, such as chloroform, methanol, and dimethyl sulfoxide. The iodonium salt 7aa does not decompose even at 70 °C, and further

Synthesis and properties of 6-alkynyl-5-aryluracils

• Ruben Manuel Figueira de Abreu,
• Till Brockmann,
• Alexander Villinger,
• Peter Ehlers and
• Peter Langer

Beilstein J. Org. Chem. 2024, 20, 898–911, doi:10.3762/bjoc.20.80

• performed on a Bruker Apex Kappa-II CCD diffractometer. The solvents used, dimethyl sulfoxide and 1,4-dioxane, were purchased as dry solvents and applied without further purification. Other reagents, catalysts, ligands, acids, and bases were used as purchased from commercial suppliers. Column chromatography

Ortho-ester-substituted diaryliodonium salts enabled regioselective arylocyclization of naphthols toward 3,4-benzocoumarins

• Ke Jiang,
• Cheng Pan,
• Limin Wang,
• Hao-Yang Wang and
• Jianwei Han

Beilstein J. Org. Chem. 2024, 20, 841–851, doi:10.3762/bjoc.20.76

• solvents including dimethyl sulfoxide (DMSO), N,N-dimethylformamide (DMF), toluene, acetic acid (AcOH) and water (Table 1, entries 9–13) were carried out. However, polar solvents such as AcOH and H2O were proved to be unsuitable for this reaction. For catalysts, we found that Cu(OAc)2 gave the best results

Regioselective quinazoline C2 modifications through the azide–tetrazole tautomeric equilibrium

• Dāgs Dāvis Līpiņš,
• Andris Jeminejs,
• Una Ušacka,
• Anatoly Mishnev,
• Māris Turks and
• Irina Novosjolova

Beilstein J. Org. Chem. 2024, 20, 675–683, doi:10.3762/bjoc.20.61

• % purity) [26] provided a more selective reaction, no water-based work-up was needed and the pure product was obtained by simple recrystallization from ethanol in yields up to 88%. The oxidation step thiol → sulfoxide was fast and full conversion to the intermediate was achieved in one hour for most

• substrates, but the step sulfoxide → sulfone was entirely slower and required stirring overnight (except for 8d (R = iC3H7)). With 2-chloro-6,7-dimethoxy-4-sulfonylquinazolines 8 in hand, we started to explore the reactivity in SNAr reactions (Scheme 5). Sulfonyl group dance reactions did not work in

Switchable molecular tweezers: design and applications

• Pablo Msellem,
• Maksym Dekthiarenko,
• Nihal Hadj Seyd and
• Guillaume Vives

Beilstein J. Org. Chem. 2024, 20, 504–539, doi:10.3762/bjoc.20.45

Synthesis of 2,2-difluoro-1,3-diketone and 2,2-difluoro-1,3-ketoester derivatives using fluorine gas

• Alexander S. Hampton,
• David R. W. Hodgson,
• Graham McDougald,
• Linhua Wang and
• Graham Sandford

Beilstein J. Org. Chem. 2024, 20, 460–469, doi:10.3762/bjoc.20.41

• difluoromethylphenyl sulfoxide offer the possibility of transferring difluoromethylene groups directly into organic systems [19][20][21][22][23][24][25] and there is now a very extensive literature on carbon–carbon bond-forming reactions using these and other difluoromethylated building blocks [3][26][27][28][29][30

Synthesis of π-conjugated polycyclic compounds by late-stage extrusion of chalcogen fragments

• Aissam Okba,
• Pablo Simón Marqués,
• Kyohei Matsuo,
• Naoki Aratani,
• Hiroko Yamada,
• Gwénaël Rapenne and
• Claire Kammerer

Beilstein J. Org. Chem. 2024, 20, 287–305, doi:10.3762/bjoc.20.30

• and the related sulfoxide 4, it was first demonstrated that electron injection is able to trigger S- (or SO-) extrusion, electrochemically but also chemically, employing decamethylcobaltocene CoCp*2 as a reducing agent (Scheme 4, top). Under the latter conditions, the target PBI compound 6a was

• obtained in 89% yield on a ≈10 mg scale from its sulfoxide precursor 4a. In anticipation of device fabrication, activation methods which do not require the addition of chemical reagents were next tested. Thermally-induced S-extrusion was first investigated by means of thermogravimetric analysis: the

• thiepine precursor 3a exhibited a mass decrease at 300 °C in agreement with the expected elimination of sulfur to yield almost quantitatively the corresponding PBI 6a. Its sulfoxide analogue 4a exhibited higher thermal reactivity, with the loss of SO identified at lower temperature (225 °C). As a proof of

Nucleophilic functionalization of thianthrenium salts under basic conditions

• Xinting Fan,
• Duo Zhang,
• Xiangchuan Xiu,
• Bin Xu,
• Yu Yuan,
• Feng Chen and
• Pan Gao

Beilstein J. Org. Chem. 2024, 20, 257–263, doi:10.3762/bjoc.20.26

• introduced a pioneering method for synthesizing air- and moisture-stable arylthianthrenium salts [11]. This novel approach involves the utilization of tetra-fluorothianthrene sulfoxide (TFT=O) or thianthrene sulfoxide (TT=O), which react with arenes under mild conditions, exhibiting exclusive

• -metal-catalyzed cross-coupling [32][33] and aminofunctionalization [34] of alkenes were achieved, benefiting from the unique reactivity of organothianthrenium species that are generated through the reaction of alkenes and thianthrene sulfoxide (TT=O) or thianthrene (TT) (Scheme 1b). Alcohols are widely