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Metal-Free Intermolecular C–H Borylation of N-Heterocycles at B–B Multiple Bonds

Brückner, Tobias, Ritschel, Benedikt, Jiménez-Halla, J. Oscar C., Fantuzzi, Felipe, Duwe, Dario, Markl, Christian, Dewhurst, Rian D., Dietz, Maximilian, Braunschweig, Holger (2023) Metal-Free Intermolecular C–H Borylation of N-Heterocycles at B–B Multiple Bonds. Angewandte Chemie International Edition, 62 (5). Article Number e202213284. ISSN 1433-7851. (doi:10.1002/anie.202213284) (KAR id:98590)


Carbene-stabilized diborynes of the form LBBL (L = NHC or CAAC) induce rapid, high yielding, intermolecular ortho-C–H borylation at N-heterocycles at room temperature. A simple pyridyldiborene is formed when an NHC-stabilized diboryne is combined with pyridine, while a CAAC-stabilized diboryne leads to activation of two pyridine molecules to give a tricyclic alkylideneborane, which can be forced to undergo a further H-shift resulting in a zwitterionic, doubly benzo-fused 1,3,2,5-diazadiborinine by heating. Use of the extended N-heteroaromatic quinoline leads to a borylmethyleneborane under mild conditions via an unprecedented boron-carbon exchange process.

Item Type: Article
DOI/Identification number: 10.1002/anie.202213284
Subjects: Q Science > QD Chemistry
Divisions: Divisions > Division of Natural Sciences > Chemistry and Forensics
Funders: European Research Council (
Deutsche Forschungsgemeinschaft (
Coordenação de Aperfeicoamento de Pessoal de Nível Superior (
Alexander von Humboldt Foundation (
Depositing User: Felipe Fantuzzi
Date Deposited: 01 Dec 2022 01:34 UTC
Last Modified: 04 Mar 2024 19:38 UTC
Resource URI: (The current URI for this page, for reference purposes)

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