Chemoselective palladium-catalyzed α-allylation of α-boryl aldehydes

Jeffrey D. St. Denis; Zhi He; Andrei K. Yudin

doi:10.1039/C2OB26503F

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Organic & Biomolecular Chemistry

Issue 39, 2012

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Chemoselective palladium-catalyzed α-allylation of α-boryl aldehydes

Jeffrey D. St. Denis,^a Zhi He^a and Andrei K. Yudin*^a

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Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Canada
E-mail: ayudin@chem.utoronto.ca ;
Fax: (+1)416-946-7676

Org. Biomol. Chem., 2012,10, 7900-7902

DOI: 10.1039/C2OB26503F
Received 19 Jul 2012, Accepted 02 Aug 2012
First published online 03 Aug 2012

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Herein we report the development of an α-allylation reaction of α-boryl aldehydes that preserves the carbon–boron bond under Pd⁰/Pd^II catalysis. A variety of α-boryl aldehydes and allylic alcohols participate in this chemoselective transformation. The α-allylated products were obtained as single regioisomers.

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