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Synfacts 2017; 13(05): 0495
DOI: 10.1055/s-0036-1590330
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Palladium-Catalyzed Reductive Heck Reaction

Contributor(s):
Mark Lautens
,
Ivan Franzoni
Kong W. Wang Q. Zhu J. * École Polytechnique Fédérale de Lausanne, Switzerland
Water as a Hydride Source in Palladium-Catalyzed Enantioselective Reductive Heck Reactions.

Angew. Chem. Int. Ed. 2017;
56: 3987-3991
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Publication History

Publication Date:
18 April 2017 (online)

 
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Key words

palladium catalysis - reductive Heck reaction - oxindoles - hydride source

Significance

Water represents the cheapest and most environmentally benign source of hydrogen or hydride; therefore, its use in combination with transition-metal catalysis is very appealing. In the present work, the authors present a palladium-catalyzed enantioselective reductive Heck reaction using water as final hydride donor.


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Comment

N-Aryl acrylamides reacted in the presence of a [PdCl2(MeCN)2] catalyst and (S)-t-BuPHOX ligand to generate the corresponding products in good yields and good enantioselectivities using water as hydride source. The use of DABCO as a base and a catalytic amount of B2(OH)4 was found to be crucial for the success of the transformation. The use of deuterium oxide allowed the synthesis of D-labeled oxindoles with >90% D incorporation.


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