Trapping of a Borirane Intermediate in the Reductive Coupling of an Arylborane to a Diborene

Journal of the American Chemical Society
Alexander HermannHolger Braunschweig

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.

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Citations

Nov 4, 2020·Chemical Communications : Chem Comm·Uwe SchmidtHolger Braunschweig
Jan 26, 2021·Angewandte Chemie·Stephan HagspielHolger Braunschweig
May 20, 2021·Chemistry : a European Journal·Felix LindlHolger Braunschweig
Jun 15, 2021·Chemical Science·Conor PranckeviciusHolger Braunschweig

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