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Synthesis of Trisubstituted Alkenyl Boronic Esters from Alkenes Using the Boryl-Heck Reaction

William B. Reid, Donald A. Watson*

*Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716, United States, Email:

W. B. Reid, D. A. Watson, Org. Lett., 2018, 20, 6822-6826.

DOI: 10.1021/acs.orglett.8b02949

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A Pd-catalyzed direct borylation of various 1,1- and 1,2-disubstituted alkenes provides trisubstituted alkenyl boronic esters with outstanding yields and excellent E/Z selectivities via a boryl-Heck pathway. Several derivatizations of the alkenyl boronic esters allow access to diverse, stereodefined, functionalized olefins.

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Direct Synthesis of Alkenyl Boronic Esters from Unfunctionalized Alkenes: A Boryl-Heck Reaction

W. B. Reid, J. J. Spillane, S. B. Krause, D. A. Watson, J. Am. Chem. Soc., 2016, 138, 5539-5542.

Key Words

Heck reaction, vinylboronates

ID: J54-Y2018