[structure: see text]. Stereochemically pure polysubstituted vinyl sulfoximines and sulfones are easily prepared by a copper-catalyzed syn carbozincation reaction of the corresponding alkynyl derivatives.
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http://dx.doi.org/10.1021/ol070070b | 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 PDFBiomed Pharmacother
November 2024
Laboratory of Immunobiology, School of Life Science, College of Natural Sciences, Kyungpook National University, 80 Daehak-ro, Buk-gu, Daegu 41566, Republic of Korea; AT-31 BIO Inc., Business Incubation Center, Kyungpook National University, 80 Daehak-ro, Buk-gu, Daegu 41566, Republic of Korea. Electronic address:
RSC 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.
View Article and Find Full Text PDFJ Med Chem
October 2024
Brain Disorders Research Center, Brain Science Research Division, Korea Institute of Science & Technology (KIST), Seoul 02792, Republic of Korea.
Multiple sclerosis (MS) is an immune-mediated neurodegenerative disease of the central nervous system (CNS), which leads to demyelination, axonal loss, and neurodegeneration. Increased oxidative stress and neurodegeneration have been implicated in all stages of MS, making neuroprotective therapeutics a promising strategy for its treatment. We previously have reported vinyl sulfones with antioxidative and anti-inflammatory properties that activate nuclear factor erythroid 2-related factor 2 (Nrf2), a transcription factor that induces the expression of cytoprotective genes against oxidative stress.
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