Chemoselective bromodeboronation of organotrifluoroborates using tetrabutylammonium tribromide: application in (Z)-dibromoalkene syntheses.
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.
Yao
Min-Liang
ML
Department of Chemistry, The University of Tennessee, Knoxville, Tennessee 37996-1600, USA.
Reddy
Marepally Srinivasa
MS
Yong
Li
L
Walfish
Ingrid
I
Blevins
David W
DW
Kabalka
George W
GW