73852-85-4Relevant articles and documents
Trapping of a Borirane Intermediate in the Reductive Coupling of an Arylborane to a Diborene
Arrowsmith, Merle,Braunschweig, Holger,Hermann, Alexander,Jiménez-Halla, J. Oscar C.,Trujillo-Gonzalez, Daniel E.,Vargas, Alfredo
, p. 5562 - 5567 (2020)
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.
Syntheses of (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)arenes through Pd-catalyzed borylation of arylbromides with the successive use of 2,2′-bis(1,3,2-benzodioxaborole) and pinacol
Takagi, Jun,Yamakawa, Tetsu
, p. 166 - 169 (2013/02/21)
Syntheses of (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)arenes through the Pd-catalyzed borylation of arylbromides with the successive use of 2,2′-bis(1,3,2-benzodioxaborole) and pinacol were investigated. PdCl 2(dppf) and AcOK in EtOH or DMSO successfully provided (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)arenes. In particular, this method was more effective in the borylation of arylbromides bearing sulfonyl groups than the conventional Pd-catalyzed borylation using pinacolborane or bis(pinacolato)diboron.