Trapping of a borirane intermediate in the reductive coupling of an arylborane to a diborene

Hermann, Alexander, Arrowsmith, Merle, Trujillo-Gonzalez, Daniel E, Jiménez-Halla, J Oscar C, Vargas, Alfredo and Braunschweig, Holger (2020) Trapping of a borirane intermediate in the reductive coupling of an arylborane to a diborene. Journal of the American Chemical Society, 142 (12). pp. 5562-5567. ISSN 0002-7863

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Abstract

The 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.

Item Type: Article
Schools and Departments: School of Life Sciences > Chemistry
Subjects: Q Science > QD Chemistry
Depositing User: Alfredo Vargas
Date Deposited: 15 Jun 2020 07:06
Last Modified: 29 Jun 2020 15:42
URI: http://sro.sussex.ac.uk/id/eprint/91892

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