Nickel-mediated hydrogenolysis of C-O bonds of aryl ethers: what is the source of the hydrogen?

J Am Chem Soc. 2012 Mar 28;134(12):5480-3. doi: 10.1021/ja300326t. Epub 2012 Mar 13.

Abstract

Mechanistic studies of the hydrogenolysis of aryl ethers by nickel were undertaken with (diphosphine)aryl methyl ethers. A Ni(0) complex containing Ni-arene interactions adjacent to the aryl-O bond was isolated. Heating led to aryl-O bond activation and generation of a nickel aryl methoxide complex. Formal β-H elimination from this species produced a nickel aryl hydride which can undergo reductive elimination in the presence of formaldehyde to generate a carbon monoxide adduct of Ni(0). The reported complexes map out a plausible mechanism of aryl ether hydrogenolysis catalyzed by nickel. Investigations of a previously reported catalytic system using isotopically labeled substrates are consistent with the mechanism proposed in the stoichiometric system, involving β-H elimination from a nickel alkoxide rather than cleavage of the Ni-O bond by H(2).

Publication types

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

MeSH terms

  • Carbon / chemistry
  • Catalysis
  • Ethers / chemistry
  • Hydrogen / chemistry*
  • Models, Molecular
  • Nickel / chemistry*
  • Oxygen / chemistry
  • Phosphines / chemistry*

Substances

  • Ethers
  • Phosphines
  • Carbon
  • Nickel
  • Hydrogen
  • Oxygen