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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:

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

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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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Boryl-Heck reaction

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

Preparation of Vinyl Silyl Ethers and Disiloxanes via the Silyl-Heck Reaction of Silyl Ditriflates

S. E. S. Martin, D. A. Watson, J. Am. Chem. Soc., 2013, 135, 13330-13333.

Key Words

Heck reaction, vinylboronates

ID: J48-Y2016