Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 46, Pages 20399-20404Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202009195
Keywords
alkenes; hydroarylation; nickel; reaction mechanisms; synthetic methods
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Funding
- Shanghai Institute of Organic Chemistry, State Key Laboratory of Organometallic Chemistry, Shanghai Rising-Star Program [20QA1411400]
- National Natural Science Foundation of China [21821002]
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Reported here is the discovery of a redox-neutral Ni-II/Ni(II)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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