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Zinc-catalyzed borylation of primary, secondary and tertiary alkyl halides with alkoxy diboron reagents at room temperature

Bose, S.K.; Fucke, K.; Liu, L.; Steel, P.G.; Marder, T.B.

Authors

S.K. Bose

K. Fucke

L. Liu

P.G. Steel

T.B. Marder



Abstract

A new catalytic system based on a ZnII NHC precursor has been developed for the cross-coupling reaction of alkyl halides with diboron reagents, which represents a novel use of a Group XII catalyst for C[BOND]X borylation. This approach gives borylations of unactivated primary, secondary, and tertiary alkyl halides at room temperature to furnish alkyl boronates, with good functional-group compatibility, under mild conditions. Preliminary mechanistic investigations demonstrated that this borylation reaction seems to involve one-electron processes.

Citation

Bose, S., Fucke, K., Liu, L., Steel, P., & Marder, T. (2014). Zinc-catalyzed borylation of primary, secondary and tertiary alkyl halides with alkoxy diboron reagents at room temperature. Angewandte Chemie International Edition, 53(7), 1799-1803. https://doi.org/10.1002/anie.201308855

Journal Article Type Article
Publication Date Feb 10, 2014
Deposit Date Feb 28, 2014
Journal Angewandte Chemie International Edition
Print ISSN 1433-7851
Electronic ISSN 1521-3773
Publisher Wiley
Peer Reviewed Peer Reviewed
Volume 53
Issue 7
Pages 1799-1803
DOI https://doi.org/10.1002/anie.201308855
Keywords Boronate esters, Cross-coupling, Homogeneous catalysis, N-heterocyclic carbenes, Suzuki–Miyaura.

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