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

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.

SUBMITTER: Reid WB

PROVIDER: S-EPMC6388719 | biostudies-literature | 2018 Nov

REPOSITORIES: biostudies-literature

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

Reid William B WB Watson Donald A DA

Organic letters 20181016 21

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. ...[more]

PMID: 30350673

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