CuI/TMEDA-catalyzed annulation of 2-bromo alkynylbenzenes with Na2S: synthesis of benzo[b]thiophenes

J Org Chem. 2011 Sep 16;76(18):7546-50. doi: 10.1021/jo201081v. Epub 2011 Aug 17.

Abstract

A copper-catalyzed thiolation annulation reaction of 2-bromo alkynylbenzenes with sodium sulfide has been developed. In the presence of CuI and TMEDA, a variety of 2-substituted benzo[b]thiophenes were readily prepared in moderate to good yields by the reaction of 2-bromo alkynylbenzenes and Na(2)S·9H(2)O.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzene / chemistry*
  • Catalysis
  • Chromatography, Thin Layer
  • Gas Chromatography-Mass Spectrometry
  • Magnetic Resonance Spectroscopy
  • Organometallic Compounds / chemistry*
  • Spectrophotometry, Infrared
  • Sulfides / chemistry*
  • Thiophenes / chemical synthesis*

Substances

  • Organometallic Compounds
  • Sulfides
  • Thiophenes
  • phenyllithium
  • Benzene
  • sodium sulfide