A versatile and highly efficient method for 1-chlorination of terminal and trialkylsilyl-protected alkynes

Chemistry. 2014 Mar 3;20(10):2746-9. doi: 10.1002/chem.201303680. Epub 2014 Feb 12.

Abstract

A highly efficient one-pot procedure for the preparation of 1-chloroalkynes and 1-chlorobutadiynes from terminal and trialkylsilyl-protected precursors is reported. This convenient reaction, proceeding under mild conditions, utilizes N-chlorosuccinimide as the chlorinating agent and tolerates a range of functional groups.

Keywords: 1-haloalkynes; chlorine; halogenation; silanes; synthetic methods.

MeSH terms

  • Alkynes / chemical synthesis*
  • Alkynes / chemistry
  • Chlorine / chemistry*
  • Halogenation
  • Molecular Structure
  • Succinimides / chemical synthesis*
  • Succinimides / chemistry
  • Trimethylsilyl Compounds / chemical synthesis*
  • Trimethylsilyl Compounds / chemistry

Substances

  • Alkynes
  • Succinimides
  • Trimethylsilyl Compounds
  • N-chlorosuccinimide
  • Chlorine