Iridium-catalyzed, intermolecular hydroetherification of unactivated aliphatic alkenes with phenols

J Am Chem Soc. 2013 Jun 26;135(25):9303-6. doi: 10.1021/ja4052153. Epub 2013 Jun 12.

Abstract

Metal-catalyzed addition of an O-H bond to an alkene is a desirable process because it allows for rapid access to ethers from abundant starting materials without the formation of waste, without rearrangements, and with the possibility to control the stereoselectivity. We report the intermolecular, metal-catalyzed addition of phenols to unactivated α-olefins. Mechanistic studies of this rare catalytic reaction revealed a dynamic mixture of resting states that undergo O-H bond oxidative addition and subsequent olefin insertion to form ether products.

Publication types

  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Alkenes / chemistry*
  • Catalysis
  • Ethers / chemical synthesis*
  • Ethers / chemistry
  • Iridium / chemistry*
  • Molecular Structure
  • Organometallic Compounds / chemistry*
  • Phenols / chemistry*

Substances

  • Alkenes
  • Ethers
  • Organometallic Compounds
  • Phenols
  • Iridium