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Synlett
DOI: 10.1055/a-2711-1420
DOI: 10.1055/a-2711-1420
Synpacts
Ni-Catalyzed Addition of Arylborons to Alkenes for the Synthesis of Quaternary Carbon Centers
Authors
Supported by: National Key Research and Development Program of China 2021YFF0701600
Supported by: Science and Technology Commission of Shanghai Municipality 24ZR1479000
Supported by: National Natural Science Foundation of China 22171280,22325110,22401288,92256303
Supported by: Program of Shanghai Academic Research Leader 22XD1424900
Funding Information This work was supported by the National Key R&D Program of China (2021YFF0701600); the National Natural Science Foundation of China (22325110, 92256303, 22171280, 22401288); the Program of Shanghai Academic Research Leader (22XD1424900); the Shanghai Science and Technology Committee (24ZR1479000); and the CAS Youth Interdisciplinary Team (JCTD-2021-11).
Abstract
All-carbon quaternary centers are prevalent structural motifs, thus attracting increasing interest from the organic community. We present here a nickel-catalyzed, Markovnikov-selective addition of stable organoborons to simple alkenes, enabled by a diimine ligand. This robust method provides efficient access to quaternary carbon centers with high yields. Furthermore, with a bulky chiral diimine ligand, quaternary carbon stereocenters can be readily prepared. Mechanistic investigations indicate the involvement of an unusual nickel migration from an alkyl nickel to an aryl nickel species.
Keywords
Quaternary carbon centers - Nickel catalysis - Diimine ligand - Addition reaction - OrganoboronsPublication History
Received: 14 July 2025
Accepted after revision: 26 September 2025
Accepted Manuscript online:
26 September 2025
Article published online:
29 October 2025
© 2025. Thieme. All rights reserved.
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