4.8 Article

Difunctionalization of Alkynones by Base-Mediated Reaction with α,α-Dithioketones

Journal

ORGANIC LETTERS
Volume 23, Issue 14, Pages 5339-5343

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c01640

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Funding

  1. National Natural Science Foundation of China [21871087, 21702088]
  2. Open Research Fund of Key Laboratory of Polar Materials and Devices, Ministry of Education

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A novel 1,2-difunctionalization of alkynones has been developed via an umpolung strategy for the synthesis of tetrasubstituted olefins. The approach features excellent yields, mild reaction conditions, a broad substrate scope, and operational simplicity.
A novel 1,2-difunctionalization of alkynones via an umpolung strategy for the synthesis of tetrasubstituted olefins has been developed. This procedure is realized by a formal C-C sigma-bond cleavage reaction of cyclic alpha,alpha-dithioketones and subsequent deprotection. Notable features of this approach include excellent yields, mild reaction conditions, a broad substrate scope, and operational simplicity.

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