A new method for the synthesis of anti-Markovnikov - or -vinyl thioethers from thiosilane and terminal alkynes under visible-light-induced photoredox/nickel dual catalysis conditions is described. With a judicious choice of a simple nickel catalyst and a ligand, this strategy enables efficient and divergent access to both - or -vinyl thioethers from the same set of simple starting materials. Notably, the approach is free of odorous thiol and has excellent compatibility with functional groups and substrate scope.
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Angew Chem Int Ed Engl
December 2024
Harvard University, Chemistry and Chemical Biology, 12 Oxford St., Mallinckrodt 303N, 02138, Cambridge, UNITED STATES OF AMERICA.
Sulfenyl fluorides are organic compounds of sulfur in formal oxidation state +2 with the formula R-S-F. Although the chloride, bromide, and iodide analogues have been extensively described in the literature, arenesulfenyl fluorides remain essentially unstudied. These structures have been implicated as putative intermediates in established processes to access polyfluorinated sulfur species; however, definitive and direct evidence of their existence has not been obtained, nor has a systematic understanding of their reactivity.
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 PDFJ Org Chem
December 2024
College of Chemical Engineering, Inner Mongolia University of Technology, Hohhot 010051, China.
In this report, we have established a novel and efficient method for selectively synthesizing either vinyl sulfides or 2-methylbenzothiazoles from the reaction of CaC and disulfides. The selective synthesis of these two distinct products can be controlled by simply adjusting the amount of KS. The underlying reaction mechanism has been thoroughly investigated through control experiments, HRMS, and FTIR, which collectively support the pivotal role of a trisulfur radical anion.
View Article and Find Full Text PDFJ Am Chem Soc
December 2024
Department of Chemistry, University of Utah, 315 S 1400 E, Salt Lake City, Utah 84112, United States.
Isotopic labeling is a powerful technique extensively used in the pharmaceutical industry. By tracking isotope-labeled molecules, researchers gain unique and invaluable insights into the pharmacokinetics and pharmacodynamics of new drug candidates. Hydrogen isotope labeling is particularly important as hydrogen is ubiquitous in organic molecules in biological systems, and it can be introduced effectively through late-stage hydrogen isotope exchange (HIE).
View Article and Find Full Text PDFInt J Biol Macromol
December 2024
School of Chemistry and Chemical Engineering, Shandong University, Jinan, Shandong 250100, China. Electronic address:
Developing candidate adsorbents with high capacity and selectivity for adsorption is a critical approach to recover gold from secondary sources such as electronic waste (e-waste). This measure not only contributes to the recycling of valuable resources but also benefits environment protection and mitigates the detriment to the ecosystem. Traditional covalent organic frameworks (COFs) have garnered great potential in various fields owing to their unique structures and innate functional sites.
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