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Use of aryl chlorides as electrophiles in Pd-catalyzed alkene difunctionalization reactions.

ABSTRACT: The development of conditions that allow use of inexpensive aryl chlorides as electrophiles in Pd-catalyzed alkene carboamination and carboetherification reactions is described. A catalyst composed of Pd(OAc)(2) and S-Phos minimizes N-arylation of the substrate and prevents formation of mixtures of regioisomeric products. A number of heterocycles, including pyrrolidines, isoxazolidines, tetrahydrofurans, and pyrazolidines, are efficiently generated with this method.

SUBMITTER: Rosen BR

PROVIDER: S-EPMC2853027 | biostudies-literature | 2010 Apr

REPOSITORIES: biostudies-literature

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Use of aryl chlorides as electrophiles in Pd-catalyzed alkene difunctionalization reactions.

Rosen Brandon R BR Ney Joshua E JE Wolfe John P JP

The Journal of organic chemistry 20100401 8

The development of conditions that allow use of inexpensive aryl chlorides as electrophiles in Pd-catalyzed alkene carboamination and carboetherification reactions is described. A catalyst composed of Pd(OAc)(2) and S-Phos minimizes N-arylation of the substrate and prevents formation of mixtures of regioisomeric products. A number of heterocycles, including pyrrolidines, isoxazolidines, tetrahydrofurans, and pyrazolidines, are efficiently generated with this method. ...[more]

PMID: 20297834

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