4.8 Article

Aryne Three-Component Coupling Involving CS2 for the Synthesis of S-Aryl Dithiocarbamates

Journal

ORGANIC LETTERS
Volume 23, Issue 23, Pages 9083-9088

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c03378

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Funding

  1. Science and Engineering Research Board (SERB), Government of India [DIA/2018/000018]
  2. Indian Institute of Science (IISc)
  3. Council of Scientific & Industrial Research (CSIR)
  4. IISc

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This study demonstrates a facile synthesis of biologically important S-aryl dithiocarbamates through aryne three-component coupling, and presents preliminary mechanistic experiments. Additionally, a unique four-component coupling reaction was observed.
A facile synthesis of biologically important S-aryl dithiocarbamates has been demonstrated by the aryne three-component coupling involving CS2 and aliphatic amines. This transition-metal-free and mild reaction is scalable and operates with good functional group compatibility. Preliminary mechanistic experiments, including density functional theory studies, are also provided. Moreover, with 3-triflyloxybenzynes, a unique four-component coupling incorporating tetrahydrofuran was observed.

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