Organocatalytic, difluorocarbene-based S-difluoromethylation of thiocarbonyl compounds
نویسندگان
چکیده
منابع مشابه
Difluoromethylation and gem-difluorocyclopropenation with difluorocarbene generated by decarboxylation.
Difluoromethylation of the activated X-H bond (X = N, O and S) and aliphatic thiols, and gem-difluorocyclopropenation of alkynes with difluorocarbene generated in situ from difluoromethylene phosphobetaine (Ph3P(+)CF2CO2(-)) by decarboxylation occurred smoothly without the presence of any base or other additives.
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Introduction of a difluoromethyl (CF2H) unit into organic molecules is of specific interest in medicinal chemistry and chemical biology, as compounds with a CF2H moiety can act as an isostere to molecules having a methanol (CH2OH) unit with improved lipophilicity. Among several strategies for the synthesis of CF2H compounds available, a late-stage difluoromethylation using easy-to-handle reagen...
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The first alpha-difluoromethyl sulfoximine compound, 2, was successfully prepared by using the copper(II)-catalyzed nitrene transfer reaction. Compound 2 was found to be a novel and efficient difluoromethylation reagent for transferring the CF(2)H group to S-, N-, and C-nucleophiles. Deuterium-labeling experiments suggest that a difluorocarbene mechanism is involved in the current difluoromethy...
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Lewis acid-catalyzed reactions of oxiranes with a variety of C=S compounds yield 1,3-oxathiolanes. The ring enlargement of monosubstituted oxiranes occurs regioselectively via cleavage of the O,C(3) bond of alkyl substituted oxiranes and the O,C(2) bond of phenyl oxirane. Furthermore, the reaction proceeds with inversion of the configuration at the center of the nucleophilic attack by the S-ato...
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ژورنال
عنوان ژورنال: Journal of Fluorine Chemistry
سال: 2015
ISSN: 0022-1139
DOI: 10.1016/j.jfluchem.2014.08.013