Redox-Neutral Nickel(II) Catalysis: Hydroarylation of Unactivated Alkenes with Arylboronic Acids |
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Authors: | Dao-Ming Wang Wang Feng Dr Yichen Wu Tao Liu Prof Dr Peng Wang |
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Institution: | State key laboratory of organometallic chemistry, Center for excellence in molecular synthesis, Shanghai Institute of Organic Chemistry, CAS, 345 Lingling Road, Shanghai, 200032 P. R. China |
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Abstract: | Reported here is the discovery of a redox-neutral NiII/NiII catalytic cycle which is capable of the linear-selective hydroarylation of unactivated alkenes with arylboronic acids for the first time. This novel catalytic cycle, enabled by the use of an electron-rich diimine ligand, features broad substrate scope, and excellent functional-group and heterocycle compatibility under mild reaction conditions in the absence of additional oxidants and reductants. Mechanistic investigations using kinetic analysis and deuterium-labelling experiments revealed the protonation to be the rate-determining step in this redox-neutral catalysis, and the reversible chain-walking nature of the newly developed diimine-Ni catalyst. |
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Keywords: | alkenes hydroarylation nickel reaction mechanisms synthetic methods |
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