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Trapping of a borirane intermediate in the reductive coupling of an arylborane to a diborene
journal contribution
posted on 2023-06-07, 07:15 authored by Alexander Hermann, Merle Arrowsmith, Daniel E Trujillo-Gonzalez, J Oscar C Jiménez-Halla, Alfredo VargasAlfredo Vargas, Holger BraunschweigThe reductive coupling of a N-heterocyclic carbene (NHC)-stabilized aryldibromoborane yields a mixture of trans- and cis-diborenes in which the aryl groups are coplanar with the diborene core. Under dilute reduction conditions two diastereomers of a borirane–borane intermediate are isolated, which upon further reduction give rise to the aforementioned diborene mixture. DFT calculations suggest a mechanism proceeding via nucleophilic attack of a dicoordinate borylene intermediate on the aryl ring and subsequent intramolecular B–B bond formation.
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Publication status
- Published
File Version
- Accepted version
Journal
Journal of the American Chemical SocietyISSN
0002-7863Publisher
American Chemical SocietyExternal DOI
Issue
12Volume
142Page range
5562-5567Department affiliated with
- Chemistry Publications
Full text available
- Yes
Peer reviewed?
- Yes
Legacy Posted Date
2020-06-15First Open Access (FOA) Date
2021-03-10First Compliant Deposit (FCD) Date
2020-06-15Usage metrics
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