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Gallium (III) triflate catalyzed efficient Strecker reaction of ketones and their fluorinated analogs.

ABSTRACT: The synthesis of alpha-aminonitriles and their fluorinated analogs has been carried out in high yield and purity by the Strecker reaction from the corresponding ketones and amines with trimethylsilyl cyanide using gallium triflate in dichloromethane. Monofluoro-, difluro-, or trifluoromethyl groups can be incorporated into the alpha-aminonitrile product by varying the nature of the fluorinated ketones. Study with various fluorinated and nonfluorinated ketones reveals that the choice of proper catalyst and the solvent system (suitable metal triflates as a catalyst and dichloromethane as a solvent) plays the key role in the direct Strecker reactions of ketones.

SUBMITTER: Prakash GK

PROVIDER: S-EPMC1820647 | biostudies-literature | 2007 Mar

REPOSITORIES: biostudies-literature

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Gallium (III) triflate catalyzed efficient Strecker reaction of ketones and their fluorinated analogs.

Prakash G K Surya GK Mathew Thomas T Panja Chiradeep C Alconcel Steevens S Vaghoo Habiba H Do Clement C Olah George A GA

Proceedings of the National Academy of Sciences of the United States of America 20070228 10

The synthesis of alpha-aminonitriles and their fluorinated analogs has been carried out in high yield and purity by the Strecker reaction from the corresponding ketones and amines with trimethylsilyl cyanide using gallium triflate in dichloromethane. Monofluoro-, difluro-, or trifluoromethyl groups can be incorporated into the alpha-aminonitrile product by varying the nature of the fluorinated ketones. Study with various fluorinated and nonfluorinated ketones reveals that the choice of proper ca ...[more]

PMID: 17360416

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