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

Org Lett

Department of Chemistry and Biochemistry , University of Delaware, Newark , Delaware 19716 , United States.

Published: November 2018

The direct borylation of disubstituted alkenes is reported. These conditions allow for the conversion of a variety 1,1- and 1,2-disubstituted alkenes to trisubstituted alkenyl boronic esters with outstanding yields and excellent E/ Z selectivities. The utility of this reaction has been demonstrated with several downstream functionalization reactions, which allow access to diverse, stereodefined, functionalized olefins. Mechanistic studies are consistent with a boryl-Heck pathway.

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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6388719PMC
http://dx.doi.org/10.1021/acs.orglett.8b02949DOI Listing

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