Brückner, Tobias, Ritschel, Benedikt, Jiménez-Halla, J. Oscar C., Fantuzzi, Felipe, Duwe, Dario, Markl, Christian, Dewhurst, Rian D., Dietz, Maximilian, Braunschweig, Holger (2022) 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. (In press) (doi:10.1002/anie.202213284) (KAR id:98590)
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| Official URL: https://doi.org/10.1002/anie.202213284 |
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Abstract
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 (https://ror.org/0472cxd90)
Deutsche Forschungsgemeinschaft (https://ror.org/018mejw64) Coordenação de Aperfeicoamento de Pessoal de Nível Superior (https://ror.org/00x0ma614) Alexander von Humboldt Foundation (https://ror.org/012kf4317) |
| Depositing User: | Felipe Fantuzzi |
| Date Deposited: | 01 Dec 2022 01:34 UTC |
| Last Modified: | 20 Jan 2023 16:00 UTC |
| Resource URI: | https://kar.kent.ac.uk/id/eprint/98590 (The current URI for this page, for reference purposes) |
| Jiménez-Halla, J. Oscar C.: |  https://orcid.org/0000-0001-7354-3506 |
| Fantuzzi, Felipe: | https://orcid.org/0000-0002-8200-8262 |
| Dewhurst, Rian D.: | https://orcid.org/0000-0001-5978-811X |
| Braunschweig, Holger: | https://orcid.org/0000-0001-9264-1726 |
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