Sequential synthesis of furans from alkynes: successive ruthenium(II)- and copper(II)-catalyzed processes

Angew Chem Int Ed Engl. 2009;48(9):1681-4. doi: 10.1002/anie.200805531.

Abstract

Step in time: 2,5-Disubstituted furans can be prepared from terminal alkynes in one pot using two successive catalytic reactions (see scheme; p-TSA = para-toluenesulfonic acid). First, a 1,3-dienyl alkyl ether is produced by the dimerization of a terminal alkyne and addition of an alcohol catalyzed by [RuCp*(NCMe)(3)][PF(6)]. Then, consecutive hydrolysis and cyclization catalyzed by CuCl(2) provides the 2,5-disubstituted furan.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / chemistry*
  • Catalysis
  • Copper / chemistry*
  • Cyclization
  • Furans / chemical synthesis*
  • Furans / chemistry
  • Ruthenium / chemistry*

Substances

  • Alkynes
  • Furans
  • Copper
  • Ruthenium