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 (free Supporting Information)
see article for more reactions
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.
see article for more examples
A. F. Ward, J. P. Wolfe, Org. Lett., 2011, 13, 4728-4731.
M. B. Bertrand, J. P. Wolfe, Tetrahedron, 2005, 61, 6447-6459.