4.7 Article

Light-Promoted and Tertiary-Amine-Assisted Hydroxysulfenylation of Alkenes: Selective and Direct One-Pot Synthesis of β-Hydroxysulfides

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 86, Issue 18, Pages 12922-12931

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c01610

Keywords

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Funding

  1. National Natural Science Foundation of China [21801163]
  2. STU Scientific Research Foundation for Talents [NTF18003]
  3. Chemistry and Chemical Engineering Guangdong Laboratory [1922003]
  4. Guangdong Province Universities and Colleges Pearl River Scholar Funded Scheme 2019 (GDUPS2019)
  5. 2020 Li Ka Shing Foundation CrossDisciplinary Research Grant [2020LKSFG05A]

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This novel strategy combines light-promotion and tertiary-amine assistance to efficiently access beta-hydroxysulfides. In contrast to traditional methods, this approach offers mild reaction conditions, high efficiency, and excellent functional group tolerance.
A light-promoted and tertiary-amine-assisted strategy for efficient hydroxysulfenylation of both electron-rich and electron-deficient alkenes with thiophenols to selectively and directly access beta-hydroxysulfides in one pot is described herein. In contrast to the previously reported thiol-oxygen co-oxidation reactions, this simple and sustainable approach features mild reaction conditions, high efficiency, and excellent functional group tolerance.

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