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

ABSTRACT: We report the first example of a boryl-Heck reaction using an electrophilic boron reagent. This palladium-catalyzed process allows for the conversion of terminal alkenes to trans-alkenyl boronic esters using commercially available catecholchloroborane (catBCl). In situ transesterification allows for rapid access to a variety of boronic esters, amides, and other alkenyl boron adducts.

SUBMITTER: Reid WB

PROVIDER: S-EPMC4957246 | biostudies-literature | 2016 May

REPOSITORIES: biostudies-literature

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

Reid William B WB Spillane Jesse J JJ Krause Sarah B SB Watson Donald A DA

Journal of the American Chemical Society 20160422 17

We report the first example of a boryl-Heck reaction using an electrophilic boron reagent. This palladium-catalyzed process allows for the conversion of terminal alkenes to trans-alkenyl boronic esters using commercially available catecholchloroborane (catBCl). In situ transesterification allows for rapid access to a variety of boronic esters, amides, and other alkenyl boron adducts. ...[more]

PMID: 27104749

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