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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)



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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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Stereoselective Synthesis of Substituted 1,3-Oxazolidines via Pd-Catalyzed Carboamination Reactions of O-Vinyl-1,2-Amino Alcohols

A. F. Ward, J. P. Wolfe, Org. Lett., 2011, 13, 4728-4731.

Stereoselective synthesis of N-protected pyrrolidines via Pd-catalyzed reactions of γ-(N-acylamino) alkenes and γ-(N-Boc-amino) alkenes with aryl bromides

M. B. Bertrand, J. P. Wolfe, Tetrahedron, 2005, 61, 6447-6459.


Key Words

Pyrrolidines, Isoxazolidines, Pyrazolidines


ID: J42-Y2010-1040