Synthesis of 3,4-disubstituted 2H-benzopyrans through C-C bond formation via electrophilic cyclization

J Org Chem. 2007 Feb 16;72(4):1347-53. doi: 10.1021/jo062234s.

Abstract

The electrophilic cyclization of substituted propargylic aryl ethers by I2, ICl, and PhSeBr produces 3,4-disubstituted 2H-benzopyrans in excellent yields. This methodology results in vinylic halides or selenides under mild reaction conditions and tolerates a variety of functional groups, including methoxy, alcohol, aldehyde, and nitro groups.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzopyrans / chemical synthesis*
  • Benzopyrans / chemistry*
  • Carbon / chemistry*
  • Cyclization
  • Electrochemistry
  • Molecular Structure

Substances

  • Benzopyrans
  • Carbon