A Versatile Room-Temperature Route to Di- and Trisubstituted Allenes Using Flow-Generated Diazo Compounds

Angew Chem Int Ed Engl. 2015 Jun 26;54(27):7920-3. doi: 10.1002/anie.201501538. Epub 2015 May 26.

Abstract

A copper-catalyzed coupling reaction between flow-generated unstabilized diazo compounds and terminal alkynes provides di- and trisubstituted allenes. This extremely mild and rapid transformation is highly tolerant of several functional groups.

Keywords: allenes; carbenes; copper; diazo compounds; flow chemistry.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkadienes / chemical synthesis*
  • Alkadienes / chemistry
  • Alkynes / chemistry*
  • Catalysis
  • Copper / chemistry*
  • Diazonium Compounds / chemistry*
  • Methane / analogs & derivatives
  • Methane / chemistry
  • Temperature

Substances

  • Alkadienes
  • Alkynes
  • Diazonium Compounds
  • carbene
  • propadiene
  • Copper
  • Methane