Synthesis of 2,3-disubstituted benzo[b]selenophenes via electrophilic cyclization

J Org Chem. 2006 Mar 17;71(6):2307-12. doi: 10.1021/jo0524268.

Abstract

2,3-Disubstituted benzo[b]selenophenes have been prepared by the electrophilic cyclization of various 1-(1-alkynyl)-2-(methylseleno)arenes by Br2, NBS, I2, ICl, PhSeCl, PhSeBr, and Hg(OAc)2. This method tolerates a wide variety of functional groups, including alcohol, ester, nitrile, nitro, and silyl groups, and proceeds under exceptionally mild reaction conditions.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Cyclization
  • Magnetic Resonance Spectroscopy / methods
  • Molecular Structure
  • Organoselenium Compounds / chemical synthesis*
  • Organoselenium Compounds / chemistry
  • Sensitivity and Specificity

Substances

  • Organoselenium Compounds