Rh catalyzed olefination and vinylation of unactivated acetanilides

J Am Chem Soc. 2010 Jul 28;132(29):9982-3. doi: 10.1021/ja103834b.

Abstract

In the catalyzed oxidative olefination of acetanilides (oxidative-Heck coupling), Rh offers great advantages over more common Pd catalysts. Lower catalyst loadings, large functional group tolerance (in particular to halides), and higher reactivity of electron-neutral olefins (styrenes) are some of the attractive features. Most interestingly, even ethylene reacts to yield the corresponding acetanilido-styrene. Moreover, the Cu(II) oxidant can also be utilized in catalytic amounts with air serving as the terminal oxidant.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetanilides / chemistry*
  • Alkenes / chemistry*
  • Catalysis
  • Isomerism
  • Rhodium / chemistry*

Substances

  • Acetanilides
  • Alkenes
  • Rhodium
  • acetanilide