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Trifluoromethylthiolation of -Chloroaldehydes: Access to Quaternary SCF3-Containing Centers

Gelat, Fabien and Poisson, Thomas and Biju, Akkattu T and Pannecoucke, Xavier and Besset, Tatiana (2018) Trifluoromethylthiolation of -Chloroaldehydes: Access to Quaternary SCF3-Containing Centers. In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (27-28,). pp. 3693-3696.

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Official URL: https://dx.doi.org/10.1002/ejoc.201800418


In this study, a straightforward methodology was developed to access quaternary -trifluoromethylthiolated chloroaldehydes. Using the Munavalli reagent as the electrophilic SCF3 source, a base-catalyzed trifluoromethylthiolation reaction with a panel of -chloroaldehydes was successfully achieved under mild reaction conditions. The -trifluoromethylthiolated chloroaldehydes were obtained in moderate to high yields (up to 88%). This approach demonstrated a good functional-group tolerance and offered access to highly functionalized quaternary trifluoromethylthiolated aldehydes, inaccessible so far. The development of an enantioselective version was investigated by using a chiral phase-transfer catalyst, giving the enantioenriched product in moderate enantiomeric excess.

Item Type: Journal Article
Additional Information: Copyright of this article belong to WILEY-V C H VERLAG GMBH, POSTFACH 101161, 69451 WEINHEIM, GERMANY
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Depositing User: Id for Latest eprints
Date Deposited: 08 Aug 2018 15:45
Last Modified: 08 Aug 2018 15:45
URI: http://eprints.iisc.ac.in/id/eprint/60361

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