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Synfacts 2010(6): 0697-0697  
DOI: 10.1055/s-0029-1219773
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Chemoselective Bromodeboronation of Organotrifluoroborates

Contributor(s): Paul Knochel, Stefan Wunderlich
M.-L. Yao, M. Srinivasa Reddy, L. Yong, I. Walfish, D. W. Blevins, G. W. Kabalka*
The University of Tennessee, Knoxville and State University of New York at New Paltz, USA
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Publication History

Publication Date:
20 May 2010 (online)

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Significance

Tetrabutylammonium tribromide (TBATB) has been found to be an efficient bromodeboronation reagent for organotrifluoroborates. The mild and metal-free reaction conditions tolerate a broad range of functional groups like carbonyl or nitro 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 this procedure.