4.8 Article

Dual gold and photoredox catalysis: visible light-mediated intermolecular atom transfer thiosulfonylation of alkenes

Journal

CHEMICAL SCIENCE
Volume 8, Issue 4, Pages 2610-2615

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c6sc05093j

Keywords

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Funding

  1. Natural Science Foundation of China
  2. Shandong province [21572118, JQ201505]
  3. fundamental research and subject construction funds [2014JC008, 104.205.2.5]
  4. Shandong University

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Regioselective difunctionalization of alkenes has attracted significant attention from synthetic chemists and has the advantage of introducing diverse functional groups into vicinal carbons of common alkene moieties in a single operation. Herein, we report an unprecedented intermolecular atom transfer thiosulfonylation reaction of alkenes by combining gold catalysis and visible-light photoredox catalysis. A trifluoromethylthio group (SCF3) and other functionalized thio groups together with a sulfonyl group were regioselectively introduced into alkenes in the most atom economical manner. A detailed mechanism study indicated that a synergistic combination of gold catalysis and photoredox catalysis is crucial for this reaction.

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