Bi(OTf)3-mediated cycloisomerization of γ-alkynyl arylketones: application to the synthesis of substituted furans

Org Lett. 2015 Mar 6;17(5):1264-7. doi: 10.1021/acs.orglett.5b00246. Epub 2015 Feb 19.

Abstract

A novel Bi(OTf)3-mediated cycloisomerization of γ-alkynyl arylketones 4, 7, or 10 with molecular sieve (MS) in MeNO2 affords 3-substituted furans 3, 8, or 11 at rt for 3 h in moderate to good yields. The method provides mild, less-toxic, atom-economic and efficient conditions. The mechanism has been studied and proposed. Moreover, this route can be enlarged to gram scale.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / chemistry
  • Cyclization
  • Furans / chemical synthesis*
  • Furans / chemistry
  • Isomerism
  • Ketones / chemistry
  • Mesylates / chemistry*
  • Molecular Structure
  • Stereoisomerism

Substances

  • Alkynes
  • Furans
  • Ketones
  • Mesylates
  • Bi(OTf)3