Oxidative Addition of Aryl Halides to a Triphosphine Ni(0) Center to Form Pentacoordinate Ni(II) Aryl Species

Oxidative addition of aryl halides to Ni(0) is a ubiquitous elementary step in cross-coupling and related reactions, usually producing a square-planar Ni­(II)–aryl intermediate. Here we show that a triphosphine ligand supports oxidative addition at a tris-ligated Ni(0) center to cleanly form stable...

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Bibliographic Details
Published in:Organometallics 2020-04, Vol.39 (8), p.1139-1144
Main Authors: Pérez−García, Pablo M, Darù, Andrea, Scheerder, Arthur R, Lutz, Martin, Harvey, Jeremy N, Moret, Marc-Etienne
Format: Article
Language:English
Subjects:
Communication
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Summary:Oxidative addition of aryl halides to Ni(0) is a ubiquitous elementary step in cross-coupling and related reactions, usually producing a square-planar Ni­(II)–aryl intermediate. Here we show that a triphosphine ligand supports oxidative addition at a tris-ligated Ni(0) center to cleanly form stable five-coordinate Ni­(II)–aryl compounds. Kinetic and computational studies support a concerted, two-electron mechanism rather than radical halogen abstraction. These results support the idea that oxidative addition to triphosphine Ni(0) species may be more generally involved in Ni/phosphine catalytic systems.
ISSN:0276-7333
1520-6041
DOI:10.1021/acs.organomet.0c00060