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.

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
• Public URL: https://durham-repository.worktribe.com/output/1383509