Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 60, Issue 6, Pages 2963-2968Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202014167
Keywords
Biradical; Boron carbonyl complex; density functional calculations; Rearrangement; Reduction
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Funding
- Deutsche Forschungsgemeinschaft under the Individual Research Grants programme
- Deutsche Forschungsgemeinschaft under Research Training Groups programme [GRK2112]
- CoordenacAo de Aperfeicoamento de Pessoal de Nivel Superior (CAPES)
- Alexander von Humboldt (AvH) Foundation
- Projekt DEAL
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The one-electron reduction of a cyclic (alkyl)(amino)carbene (CAAC)-stabilized arylborylene carbonyl complex yields a dimeric borylketyl radical anion, leading to a highly nucleophilic dianionic (boraneylidene)methanolate. Computational analyses support the existence of a radical anion intermediate in this process.
The one-electron reduction of a cyclic (alkyl)(amino)carbene (CAAC)-stabilized arylborylene carbonyl complex yields a dimeric borylketyl radical anion, resulting from an intramolecular aryl migration to the CO carbon atom. Computational analyses support the existence of a [(CAAC)B(CO)Ar](.-) radical anion intermediate. Further reduction leads to a highly nucleophilic dianionic (boraneylidene)methanolate.
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