Iron-catalyzed synthesis of functionalized 2H-chromenes via intramolecular alkyne-carbonyl metathesis

J Org Chem. 2011 May 6;76(9):3539-44. doi: 10.1021/jo2000012. Epub 2011 Mar 31.

Abstract

An iron-catalyzed intramolecular alkyne-aldehyde metathesis strategy of the alkynyl ether of salicylaldehyde derivatives has been developed which works under mild reaction conditions to produce the functionalized 2H-chromene derivatives. This protocol is compatible toward a wide range of functional groups, such as methoxy, fluoro, chloro, bromo, and phenyl groups. This method provides an atom-economical and environmentally friendly approach for the synthesis of a series of substituted 2H-chromenes.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry*
  • Alkynes / chemistry*
  • Benzopyrans / chemical synthesis*
  • Benzopyrans / chemistry*
  • Catalysis
  • Green Chemistry Technology / methods*
  • Iron / chemistry*

Substances

  • Aldehydes
  • Alkynes
  • Benzopyrans
  • Iron