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

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...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2016-05, Vol.138 (17), p.5539-5542
Main Authors: Reid, William B, Spillane, Jesse J, Krause, Sarah B, Watson, Donald A
Format: Article
Language:English
Subjects:
Alkenes - chemistry
Boron Compounds - chemical synthesis
Boron Compounds - chemistry
Esters - chemical synthesis
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Summary: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.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.6b02914