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

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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… Click to show full abstract

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.

Keywords: synthesis trisubstituted; boryl heck; reaction; boronic esters; alkenyl boronic; trisubstituted alkenyl

Journal Title: Organic letters
Year Published: 2018

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