Practical Ni-Catalyzed Aryl-Alkyl Cross-Coupling of Secondary Redox-Active Esters

J Am Chem Soc. 2016 Feb 24;138(7):2174-7. doi: 10.1021/jacs.6b00250. Epub 2016 Feb 9.

Abstract

A new transformation is presented that enables chemists to couple simple alkyl carboxylic acids with aryl zinc reagents under Ni-catalysis. The success of this reaction hinges on the unique use of redox-active esters that allow one to employ such derivatives as alkyl halides surrogates. The chemistry exhibits broad substrate scope and features a high degree of practicality. The simple procedure and extremely inexpensive nature of both the substrates and pre-catalyst (NiCl2·6H2O, ca. $9.5/mol) bode well for the immediate widespread adoption of this method.

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

  • Carboxylic Acids / chemistry*
  • Catalysis
  • Esters / chemical synthesis
  • Esters / chemistry*
  • Molecular Structure
  • Nickel / chemistry*
  • Organometallic Compounds / chemistry*
  • Oxidation-Reduction

Substances

  • Carboxylic Acids
  • Esters
  • Organometallic Compounds
  • Nickel