4.8 Article

Modular Synthesis of Sulfonyl Benzoheteroles by Silver-Catalyzed Heteroaromatization of Propargylic Alcohols with p-Toluenesulfonylmethyl Isocyanide (TosMIC): Dual Roles of TosMIC

Journal

ORGANIC LETTERS
Volume 16, Issue 23, Pages 6204-6207

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol5031316

Keywords

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Funding

  1. NSFC [21172029, 21202016, 21372038]
  2. MEPRC [NCET-13-0714]
  3. Jilin Provincial Research Foundation for Basic Research [20140519008JH]

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A new silver-catalyzed heteroaromatization of propargylic alcohols with p-toluenesulfonylmethyl isocyanide (TosMIC) has been developed that provides an efficient and modular approach to sulfonyl benzoheteroles. For the first time, TosMIC plays a dual role in one reaction: sulfonyl source and ligand. An unprecedented deoxysulfonylation/hydration/condensation reaction pathway is disclosed.

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