-Alkyl sulfoximines react with arynes generated under mild conditions providing -sulfinylanilines in good yields. The transformation is characterized by a broad substrate scope and a good functional group tolerance. The structure of a reaction product was confirmed by single-crystal X-ray diffraction.
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http://dx.doi.org/10.1021/acs.joc.3c00012 | DOI Listing |
Angew Chem Int Ed Engl
January 2025
Osaka University: Osaka Daigaku, Department of Applied Chemistry, JAPAN.
Although numerous transition-metal catalyzed cross-coupling reactions of alkenyl electrophiles with a sulfur(VI) leaving group, mainly alkenyl sulfones, have been developed, most rely heavily on highly nucleophilic Grignard reagents, and the use of organoboron reagents remains challenging. We report herein facile preparation and the following Pd-catalyzed Suzuki-Miyaura cross-coupling reaction of alkenyl sulfoximine, a monoaza analog of sulfone. The condensation of alkyl sulfoximine with aldehydes, developed in this study, makes alkenyl sulfoximines more readily available.
View Article and Find Full Text PDFChemistry
December 2024
Cardiff Catalysis Institute, School of Chemistry, Cardiff University, Translational Research Hub, Maindy Road, Cathays, Cardiff, Cymru/Wales, CF24 4HQ, UK.
Precise control of selective alkene functionalization is a continuing challenge in the chemical community. In this study, we develop a substitution-controlled regiodivergent thioetherification of di- or trisubstituted alkenes using 10 mol % tris(pentafluorophenyl)borane [B(CF)] as a catalyst and N-thiosuccinimide as a sulfenylating reagent. This metal-free borane catalyzed C-S bond forming method is utilized for a Csp-H sulfenylation reaction to synthesize an array of diphenylvinylsulfide derivatives with good to excellent yields (25 examples, up to 91 % yield).
View Article and Find Full Text PDFOrg Lett
December 2024
Key Laboratory of Novel Targets and Drug Study for Neural Repair of Zhejiang Province, School of Medicine, Hangzhou City University, Hangzhou 310015, Zhejiang, P. R. China.
A Pd/norbornene-mediated three-component modular one-step reaction facilitated by dual C-H bond activation and cascade cyclization is reported. This procedure uses norbornene as a catalyst in the Catellani-type reaction and as an alkylating building block to accomplish the dual unactivated C-H bond functionalization protocol, which results in the production of polyheterocyclic eight-membered sulfoximines with an indene-fused moiety. This mild, scalable protocol's wide substrate range makes it ideal for site-selective dual C-H functionalization at the highly chemoselective aryl sites.
View Article and Find Full Text PDFChemistry
January 2025
Institute of Chemistry, University of Tartu, Ravila 14a Str, Tartu, 50411, Estonia.
Despite the numerous published syntheses and applications of sulfoximines, very few studies describe their physico-chemical properties and in particular their acidic, basic and lipophilic or hydrophilic characters. We report for the first time the acidity values (pK) of fluorinated sulfoximines in water and in acetonitrile, as well as the basicity (pK) measurements of fluorinated and non-fluorinated sulfoximines in acetonitrile. The same sulfoximine library was also studied in terms of lipophilicity with measurement of the Hansch parameters of the sulfoximine moieties.
View Article and Find Full Text PDFRSC Adv
September 2024
University of Ljubljana, Faculty of Chemistry and Chemical Technology Večna pot 113 1000 Ljubljana Slovenia
The oxidation of various structurally different -trifluoromethylthio sulfoximines was investigated using different oxidizing agents and conditions. Mono- and disubstituted phenyl methyl and phenyl cyclopropyl -trifluoromethylthio sulfoximines were oxidized with NaOCl·5HO in water, while sterically hindered substrates bearing bulkier alkyl chains or two phenyl rings required the addition of MeCN to the reaction mixture. Chloro-, bromo-, and cyano-substituted substrates, as well as substrates bearing the benzyl groups, required a completely different approach using -CPBA in DCM.
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