Challenging nickel-catalysed amine arylations enabled by tailored ancillary ligand design

Christopher M. Lavoie, Preston M. MacQueen, Nicolas L. Rotta-Loria, Ryan S. Sawatzky, Andrey Borzenko, Alicia J. Chisholm, Breanna K. V. Hargreaves, Robert McDonald, Michael J. Ferguson and Mark Stradiotto ()
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Christopher M. Lavoie: Dalhousie University
Preston M. MacQueen: Dalhousie University
Nicolas L. Rotta-Loria: Dalhousie University
Ryan S. Sawatzky: Dalhousie University
Andrey Borzenko: Dalhousie University
Alicia J. Chisholm: Dalhousie University
Breanna K. V. Hargreaves: Dalhousie University
Robert McDonald: X-Ray Crystallography Laboratory, University of Alberta
Michael J. Ferguson: X-Ray Crystallography Laboratory, University of Alberta
Mark Stradiotto: Dalhousie University

Nature Communications, 2016, vol. 7, issue 1, 1-11

Abstract: Abstract Palladium-catalysed C(sp2)–N cross-coupling (that is, Buchwald–Hartwig amination) is employed widely in synthetic chemistry, including in the pharmaceutical industry, for the synthesis of (hetero)aniline derivatives. However, the cost and relative scarcity of palladium provides motivation for the development of alternative, more Earth-abundant catalysts for such transformations. Here we disclose an operationally simple and air-stable ligand/nickel(II) pre-catalyst that accommodates the broadest combination of C(sp2)–N coupling partners reported to date for any single nickel catalyst, without the need for a precious-metal co-catalyst. Key to the unprecedented performance of this pre-catalyst is the application of the new, sterically demanding yet electron-poor bisphosphine PAd-DalPhos. Featured are the first reports of nickel-catalysed room temperature reactions involving challenging primary alkylamine and ammonia reaction partners employing an unprecedented scope of electrophiles, including transformations involving sought-after (hetero)aryl mesylates for which no capable catalyst system is known.

Date: 2016
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DOI: 10.1038/ncomms11073

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