4.2 Article

N-Propargylation of secondary amines directly using calcium carbide as an acetylene source

Journal

JOURNAL OF CHEMICAL RESEARCH
Volume -, Issue 6, Pages 341-345

Publisher

SCIENCE REVIEWS 2000 LTD
DOI: 10.3184/174751917X14949427622099

Keywords

N-propargylation; secondary amine; calcium carbide; acetylene source; propargylic tertiary amine

Funding

  1. National Natural Science Foundation of China [21462038, 21362034]
  2. Key Laboratory of Eco-Environment-Related Polymer Materials for Ministry of Education

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A one-pot N-propargylation of secondary amines has been achieved by heating the amine with formaldehyde and calcium carbide in DMSO in the presence of CuCl as a catalyst. Fifteen examples of propargylic tertiary amines, 12 of which are novel, were efficiently prepared in yields of 65-84%. The advantages of the method are broad substrate scope and a simple work-up procedure.

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