Communication

Chasing the Proton Culprit from Palladium-Catalyzed Allylic Amination

Davenport Research Laboratories, Department of Chemistry, The University of Toronto, 80 St. George Street, Toronto, Ontario, Canada M5S 3H6
J. Am. Chem. Soc., 2007, 129 (46), pp 14172–14173
DOI: 10.1021/ja076659n
Publication Date (Web): October 26, 2007
Copyright © 2007 American Chemical Society

Abstract

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We have found that the addition of base has a significant effect on palladium-catalyzed allylic amination. The long-standing problem of controlling the branched-to-linear ratio has been solved. In the presence of DBU and inexpensive, readily available ligands, palladium-catalyzed allylation proceeds under kinetic control, leading to high branched selectivity. Given the widespread utility of palladium-catalyzed allylic amination, we expect that these findings will be relevant in many areas ranging from asymmetric catalysis to target-oriented synthesis.

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Article Views: 2,223 Times
Received 4 September 2007
Published online 26 October 2007
Published in print 1 November 2007
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