Borylated N-Heterocyclic Carbenes

  • Author: Chemistry – A European Journal
  • Published Date: 27 February 2019
  • Source / Publisher: Chemistry – A European Journal/Wiley-VCH
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA
thumbnail image: Borylated N-Heterocyclic Carbenes

Related Societies

Singlet carbenes are useful as ligands in metal catalysts and for the stabilization of unusual main group compounds. Simon Aldridge and colleagues, Oxford University, UK, have tried to use the bulky, strongly donating diazaborolyl group {(HCDippN)2B} (Dipp = 2,6-iPr2C6H3) as the N-bound substituent of N-heterocyclic carbenes (NHCs). The imidazolium salts which acts as NHC precursors were synthesized using the bromoborane {(HCDippN)2}BBr and the parent heterocycles, imidazole or benzamidazole.

An N-to-C migration of the boryl substituent prevented the isolation of an NHC with two N-bound boryl groups. Kinetic and DFT studies on the migration process suggest an intramolecular 1,2-shift. In contrast to earlier reports, it seems that such shifts are feasible in aromatic carbenes.

NHCs with a single N-bound boryl group and one methyl substituent (example pictured) could be accessed. These NHCs were characterized by NMR spectroscopy and could be trapped by metal fragments. The synthesized carbenes provide an increased electron donor ability compared with unsaturated NHCs and a large (if unsymmetrical) steric bulk. Boryl substituted carbenes are not common and, according to the team, these are the first examples of NHCs featuring an exocyclic N-boryl group.


Article Views: 1016

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

Magazine of Chemistry Europe (16 European Chemical Societies)published by Wiley-VCH