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

Jie Wang, Tian Qin, Tie Gen Chen, Laurin Wimmer, Jacob T. Edwards, Josep Cornella, Benjamin Vokits, Scott A. Shaw, Phil S. Baran

Research output: Contribution to journalArticlepeer-review

113 Scopus citations

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 H2O—$9.5 mol−1, Et3N) coupled to the virtually unlimited commercial catalog of available starting materials bodes well for its rapid adoption.

Original languageEnglish (US)
Pages (from-to)9676-9679
Number of pages4
JournalAngewandte Chemie - International Edition
Volume55
Issue number33
DOIs
StatePublished - Jan 1 2016
Externally publishedYes

Keywords

  • decarboxylation
  • homogeneous catalysis
  • nickel catalysts
  • redox-active esters
  • Suzuki cross-coupling

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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