4.4 Article

Visible-Light-Mediated ipso -Carbosulfonylation of Alkynes: Synthesis of 3-Sulfonylspiro[4,5]trienones from Propiolamides and Sulfonyl Chlorides under Transition-Metal-Free Conditions

Journal

SYNLETT
Volume 29, Issue 18, Pages 2396-2403

Publisher

GEORG THIEME VERLAG KG
DOI: 10.1055/s-0037-1609948

Keywords

spiro compounds; difunctionalization; visible-light photoredox catalysis; propiolamides; sulfonyl chlorides

Funding

  1. Scientific Research Fund of Education Department of Hunan Provincial [16A087]
  2. Natural Science Foundation of Hunan Province [2018JJ3208]
  3. National Natural Science Foundation of China [21602056]

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An efficient and convenient strategy to synthesize diverse 3-sulfonylspiro[4,5]trienones has been developed. This ipso-carbosulfonylation of alkynes proceeds by visible-light catalysis under transition-metal-free conditions and represents a new sulfonylation and ipso-cyclization of alkynes. In this transformation, the O atom in the newly generated carbonyl is derived from H2O and it features a broad substrates scope, especially for alkyl propiolamides and aliphatic sulfonyl chlorides.

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