title: Chemoselective bromodeboronation of organotrifluoroborates using tetrabutylammonium tribromide: application in (Z)-dibromoalkene syntheses.
abstract: Tetrabutylammonium tribromide (TBATB) has been found to be a unique bromodeboronation reagent for organotrifluoroborates. When compared to previously reported bromodeboronation methods, the mild and metal-free reaction conditions tolerate a wider range of functional groups. High regio- and chemoselectivity are observed in the presence of both unsaturated carbon-carbon bonds and aldehyde functional groups. An efficient synthetic route to (Z)-dibromoalkenes from terminal alkynes has been developed using the TBATB-mediated bromodeboronation as a key step.
authors.affiliation: Department of Chemistry, The University of Tennessee, Knoxville, Tennessee 37996-1600, USA.
authors.forename: Min-Liang
authors.initials: ML
authors.lastname: Yao
authors.forename: Marepally Srinivasa
authors.initials: MS
authors.lastname: Reddy
authors.forename: Li
authors.initials: L
authors.lastname: Yong
authors.forename: Ingrid
authors.initials: I
authors.lastname: Walfish
authors.forename: David W
authors.initials: DW
authors.lastname: Blevins
authors.forename: George W
authors.initials: GW
authors.lastname: Kabalka