Use of Aryl Chlorides as Electrophiles in Pd-Catalyzed Alkene Difunctionalization Reactions
Brandon R. Rosen, Joshua E. Ney and John P. Wolfe*
*Department of Chemistry, University of Michigan, 930 N. University Avenue, Ann Arbor, MI 48109-1055, USA, Email: jpwolfeumich.edu
B. R. Rosen, J. E. Ney, J. P. Wolfe, J. Org. Chem., 2010, 75, 2756-2759.
DOI: 10.1021/jo100344k
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Abstract
A catalyst composed of Pd(OAc)2 and S-Phos allows the conversion of aryl chlorides as electrophiles in Pd-catalyzed alkene carboamination and carboetherification, minimizes N-arylation, and prevents formation of regiosisomieric mixtures. Various heterocycles, including pyrrolidines, isoxazolidines, tetrahydrofurans, and pyrazolidines, are efficiently generated with this method.
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A. F. Ward, J. P. Wolfe, Org. Lett., 2011, 13, 4728-4731.
M. B. Bertrand, J. P. Wolfe, Tetrahedron, 2005, 61, 6447-6459.
Key Words
Pyrrolidines, Isoxazolidines, Pyrazolidines
ID: J42-Y2010-1040