Direct Synthesis of Alkenyl Boronic Esters from Unfunctionalized Alkenes: A Boryl-Heck Reaction
William B. Reid, Jesse J. Spillane, Sarah B. Krause and Donald A. Watson*
*Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716, United States, Email: dawatsonudel.edu
W. B. Reid, J. J. Spillane, S. B. Krause, D. A. Watson, J. Am. Chem. Soc., 2016, 138, 5539-5542.
DOI: 10.1021/jacs.6b02914 (free Supporting Information)
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A boryl-Heck reaction of terminal alkenes with commercially available catecholchloroborane (catBCl) as an electrophilic boron reagent provides trans-alkenyl boronic esters. In situ transesterification allows for rapid access to various boronic esters, amides, and other alkenyl boron adducts.
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S. E. S. Martin, D. A. Watson, J. Am. Chem. Soc., 2013, 135, 13330-13333.