Ni(COD)(DQ): An Air-Stable 18-Electron Nickel(0)-Olefin Precatalyst

Van T Tran; Zi-Qi Li; Omar Apolinar; Joseph Derosa; Matthew V Joannou; Steven R Wisniewski; Martin D Eastgate; Keary M Engle

doi:10.1002/anie.202000124

Ni(COD)(DQ): An Air-Stable 18-Electron Nickel(0)-Olefin Precatalyst

Angew Chem Int Ed Engl. 2020 May 4;59(19):7409-7413. doi: 10.1002/anie.202000124. Epub 2020 Mar 18.

Authors

Van T Tran¹, Zi-Qi Li¹, Omar Apolinar¹, Joseph Derosa¹, Matthew V Joannou², Steven R Wisniewski², Martin D Eastgate², Keary M Engle¹

Affiliations

¹ Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA, 92037, USA.
² Chemical & Synthetic Development, Bristol-Myers Squibb, 1 Squibb Drive, New Brunswick, NJ, 08903, USA.

PMID: 32065839
DOI: 10.1002/anie.202000124

Abstract

We report that Ni(COD)(DQ) (COD=1,5-cyclooctadiene, DQ=duroquinone), an air-stable 18-electron complex originally described by Schrauzer in 1962, is a competent precatalyst for a variety of nickel-catalyzed synthetic methods from the literature. Due to its apparent stability, use of Ni(COD)(DQ) as a precatalyst allows reactions to be conveniently performed without use of an inert-atmosphere glovebox, as demonstrated across several case studies.

Keywords: cross-coupling; homogeneous catalysis; nickel; precatalysts.

Publication types

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