A heterogeneous nickel catalyst for the hydrogenolysis of aryl ethers without arene hydrogenation

Alexey G Sergeev; Jonathan D Webb; John F Hartwig

doi:10.1021/ja3085912

A heterogeneous nickel catalyst for the hydrogenolysis of aryl ethers without arene hydrogenation

J Am Chem Soc. 2012 Dec 19;134(50):20226-9. doi: 10.1021/ja3085912. Epub 2012 Dec 7.

Authors

Alexey G Sergeev¹, Jonathan D Webb, John F Hartwig

Affiliation

¹ Department of Chemistry, University of California, Berkeley, Berkeley, California 94720-1460, United States.

PMID: 23163756
DOI: 10.1021/ja3085912

Abstract

A heterogeneous nickel catalyst for the selective hydrogenolysis of aryl ethers to arenes and alcohols generated without an added dative ligand is described. The catalyst is formed in situ from the well-defined soluble nickel precursor Ni(COD)(2) or Ni(CH(2)TMS)(2)(TMEDA) in the presence of a base additive, such as (t)BuONa. The catalyst selectively cleaves C(Ar)-O bonds in aryl ether models of lignin without hydrogenation of aromatic rings, and it operates at loadings down to 0.25 mol % at 1 bar of H(2) pressure. The selectivity of this catalyst for electronically varied aryl ethers differs from that of the homogeneous catalyst reported previously, implying that the two catalysts are distinct from each other.

Publication types

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

MeSH terms

Catalysis
Ethers / chemistry*
Hydrocarbons, Aromatic / chemistry*
Hydrogen / chemistry*
Nickel / chemistry*

Substances

Ethers
Hydrocarbons, Aromatic
Nickel
Hydrogen