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Organocatalytic Decarboxylative Cyanomethylation of Difluoromethyl and Trifluoromethyl Ketones.

ABSTRACT: An efficient organocatalytic method for the synthesis of difluoromethyl and trifluoromethyl substituted ?-hydroxynitriles is introduced. The decarboxylative cyanomethylation of fluorinated ketones with readily available cyanoacetic acid gives a variety of tertiary alcohols in high yields and without concomitant water elimination. The reaction occurs in the presence of catalytic amounts of triethylamine, can be upscaled and applied to chlorofluoromethyl ketones and difluoromethyl ketimines.

SUBMITTER: Balaraman K

PROVIDER: S-EPMC6615566 | biostudies-literature | 2018 Dec

REPOSITORIES: biostudies-literature

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Organocatalytic Decarboxylative Cyanomethylation of Difluoromethyl and Trifluoromethyl Ketones.

Balaraman Kaluvu K Moskowitz Max M Wolf Christian C

Advanced synthesis & catalysis 20180930 24

An efficient organocatalytic method for the synthesis of difluoromethyl and trifluoromethyl substituted β-hydroxynitriles is introduced. The decarboxylative cyanomethylation of fluorinated ketones with readily available cyanoacetic acid gives a variety of tertiary alcohols in high yields and without concomitant water elimination. The reaction occurs in the presence of catalytic amounts of triethylamine, can be upscaled and applied to chlorofluoromethyl ketones and difluoromethyl ketimines. ...[more]

PMID: 31289455

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