Metal-Free Carbene Insertion into B−H Bonds

  • Author:
  • Published: 07 October 2019
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA
  • Source / Publisher: Journal of the American Chemical Society/ACS Publications
  • Associated Societies: American Chemical Society (ACS), USA
thumbnail image: Metal-Free Carbene Insertion into B−H Bonds

Organoboron compounds are useful intermediates in organic synthesis. Simple, efficient ways of synthesizing organoboron compounds are, thus, interesting. While many other carbon–heteroatom (C–X) bonds can be created via the insertion of a carbene into an X–H bond, such insertions into B–H bonds are challenging.

Frank Glorius, University of Münster, Germany, and colleagues have developed a metal-free insertion of carbenes into B−H bonds, mediated by visible light. The team used electron-rich α-siloxycarbenes (pictured right), which were prepared from acylsilanes under blue light-emitting diodes (LEDs). These carbenes can then directly react with pinacolborane (HBpin) to give the desired α-alkoxyorganoboronate esters.

The reaction is atom-economical and has a broad substrate scope. It tolerates different silyl groups as well as alkyl- and aryl substituents on the α-siloxycarbenes. Almost all products were obtained in quantitative yields, and the reaction is scalable.


Article Views: 511

Sign in Area

Please sign in below

Additional Sign In options

Please note that to comment on an article you must be registered and logged in.
Registration is for free, you may already be registered to receive, e.g., the newsletter. When you register on this website, please ensure you view our terms and conditions. All comments are subject to moderation.

Article Comments - To add a comment please sign in

Bookmark and Share

If you would like to reuse any content, in print or online, from, please contact us first for permission. more

CONNECT: on Facebook on Twitter on YouTube on LinkedIn Sign up for our free newsletter

A product of ChemPubSoc Europe (16 European Chemical Societies)and Wiley-VCH