4.8 Article

Reaction of Arynes with Vinyl Sulfoxides: Highly Stereospecific Synthesis of ortho-Sulfinylaryl Vinyl Ethers

Journal

ORGANIC LETTERS
Volume 19, Issue 3, Pages 666-669

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.6b03827

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Funding

  1. China Scholarship Council
  2. Deutsche Forschungsgemeinschaft (DFG)

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The reaction of in situ generated arynes with aryl vinyl sulfoxides provides ortho-arylsulfinylaryl vinyl ethers via aryne sigma-bond insertion into the S-O-bond and concomitant stereospecific S-O-vinyl migration. The cascade allows preparing di- or trisubstituted vinyl ethers with excellent stereospecificity. The reactions proceed under mild conditions, the substrate scope is broad, and the products obtained are valuable.

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