4.8 Article

Visible light-induced C-H sulfenylation using sulfinic acids

Journal

GREEN CHEMISTRY
Volume 19, Issue 20, Pages 4785-4791

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c7gc01891f

Keywords

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Funding

  1. Natural Science Foundation of Shandong Province for Outstanding Young Scholars [ZR2016JL012, ZR2015JL004]
  2. National Natural Science Foundation of China [21302110, 21302109, 21402103, 21675099, 21772107]
  3. Taishan Scholar Foundation of Shandong Province
  4. China Postdoctoral Science Foundation [150030]
  5. Scientific Research Foundation of Qufu Normal University [BSQD 2012021]

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The visible light and Eosin B-catalyzed direct sulfenylation of sp(2) C-H bonds with sulfinic acids through a photoredox process has been demonstrated at room temperature under transition metal-free conditions for the first time. Diverse heteroaryl sulfides were obtained in moderate to good yields. This is the first example of the sulfenylation of sp(2) C-H bonds using arylsulfinic acids as odorless sulfur reagents under visible light-induced conditions. More interestingly, the reductive products could be obtained under visible light-induced oxidative conditions. This protocol demonstrates a new model for C-S bond formation, which serves as a novel approach toward the synthesis of heteroaryl sulfides.

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