Nickel-Catalyzed Cross-Coupling of Redox-Active Esters with Boronic Acids

Angew Chem Int Ed Engl. 2016 Aug 8;55(33):9676-9. doi: 10.1002/anie.201605463. Epub 2016 Jul 6.

Abstract

A transformation analogous in simplicity and functional group tolerance to the venerable Suzuki cross-coupling between alkyl-carboxylic acids and boronic acids is described. This Ni-catalyzed reaction relies upon the activation of alkyl carboxylic acids as their redox-active ester derivatives, specifically N-hydroxy-tetrachlorophthalimide (TCNHPI), and proceeds in a practical and scalable fashion. The inexpensive nature of the reaction components (NiCl2 ⋅6 H2 O-$9.5 mol(-1) , Et3 N) coupled to the virtually unlimited commercial catalog of available starting materials bodes well for its rapid adoption.

Keywords: Suzuki cross-coupling; decarboxylation; homogeneous catalysis; nickel catalysts; redox-active esters.

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

  • Boronic Acids / chemistry*
  • Catalysis
  • Esters / chemistry*
  • Molecular Structure
  • Nickel / chemistry*
  • Oxidation-Reduction

Substances

  • Boronic Acids
  • Esters
  • Nickel