Synthesis and Reactivity of Paramagnetic Nickel Polypyridyl Complexes Relevant to C(sp2)–C(sp3)Coupling Reactions

A number of new transition metal catalyzed methods for the formation of C(sp2)–C(sp3) bonds have recently been described. These reactions often utilize bidentate polypyridyl‐ligated Ni catalysts, and paramagnetic NiI halide or aryl species are proposed in the catalytic cycles. However, there is litt...

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Published in:Angewandte Chemie (International ed.) 2019-04, Vol.58 (18), p.6094-6098
Main Authors: Mohadjer Beromi, Megan, Brudvig, Gary W., Hazari, Nilay, Lant, Hannah M. C., Mercado, Brandon Q.
Format: Article
Language:English
Subjects:
Aromatic compounds
Catalysis
Catalysts
Catalytic activity
Chemical reactions
Coupling
cross-electrophile coupling
Nickel
nickel(I) Complexes
polypyridyl ligands
reaction mechanism
Synthesis
Transition metals
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Summary:A number of new transition metal catalyzed methods for the formation of C(sp2)–C(sp3) bonds have recently been described. These reactions often utilize bidentate polypyridyl‐ligated Ni catalysts, and paramagnetic NiI halide or aryl species are proposed in the catalytic cycles. However, there is little knowledge about complexes of this type. Here, we report the synthesis of paramagnetic bidentate polypyridyl‐ligated Ni halide and aryl complexes through elementary reactions proposed in catalytic cycles for C(sp2)–C(sp3) bond formation. We investigate the ability of these complexes to undergo organometallic reactions that are relevant to C(sp2)–C(sp3) coupling through stoichiometric studies and also explore their catalytic activity. The synthesis and both the stoichiometric and catalytic reactivity of polypyridyl supported NiI halide and aryl species relevant to modern C(sp2)–C(sp3) couplings is reported. The complexes can be generated through elementary reactions which are relevant to contemporary coupling reactions, and their nuclearity is dependent on the ancillary ligand.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201901866