Zinc-Catalyzed Dual C–X and C–H Borylation of Aryl Halides

Bose, Shubhankar K.; Deißenberger, Andrea; Eichhorn, Antonius; Steel, Patrick G.; Lin, Zhenyang; Marder, Todd B.

doi:10.1002/anie.201505603

Zinc-Catalyzed Dual C–X and C–H Borylation of Aryl Halides

Bose, Shubhankar K.; Deißenberger, Andrea; Eichhorn, Antonius; Steel, Patrick G.; Lin, Zhenyang; Marder, Todd B.

Authors

Shubhankar K. Bose

Andrea Deißenberger

Antonius Eichhorn

Professor Patrick Steel p.g.steel@durham.ac.uk
Professor

Zhenyang Lin

Todd B. Marder

Abstract

A zinc-catalyzed combined C[BOND]X and C[BOND]H borylation of aryl halides using B2pin2 (pin=OCMe2CMe2O) to produce the corresponding 1,2-diborylarenes under mild conditions was developed. Catalytic C[BOND]H bond activation occurs ortho to the halide groups if such a site is available or meta to the halide if the ortho position is already substituted. This method thus represents a novel use of a group XII catalyst for C[BOND]H borylation. This transformation does not proceed via a free aryne intermediate, but a radical process seems to be involved.

Citation

Bose, S. K., Deißenberger, A., Eichhorn, A., Steel, P. G., Lin, Z., & Marder, T. B. (2015). Zinc-Catalyzed Dual C–X and C–H Borylation of Aryl Halides. Angewandte Chemie International Edition, 54(40), 11843-11847. https://doi.org/10.1002/anie.201505603

Journal Article Type	Article
Acceptance Date	Jun 17, 2015
Online Publication Date	Aug 18, 2015
Publication Date	Sep 28, 2015
Deposit Date	Mar 10, 2017
Publicly Available Date	Mar 13, 2017
Journal	Angewandte Chemie International Edition
Print ISSN	1433-7851
Electronic ISSN	1521-3773
Publisher	Wiley
Peer Reviewed	Peer Reviewed
Volume	54
Issue	40
Pages	11843-11847
DOI	https://doi.org/10.1002/anie.201505603

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Copyright Statement
This is the peer reviewed version of the following article: Bose, Shubhankar K., Deißenberger, Andrea, Eichhorn, Antonius, Steel, Patrick G., Lin, Zhenyang & Marder, Todd B. (2015). Zinc-Catalyzed Dual C–X and C–H Borylation of Aryl Halides. Angewandte Chemie International Edition 54(40): 11843-11847, which has been published in final form at https://doi.org/10.1002/anie.201505603. This article may be used for non-commercial purposes in accordance With Wiley-VCH Terms and Conditions for self-archiving.