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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Abstract

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
Publication:	EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Publisher:	WILEY-V C H VERLAG GMBH, POSTFACH 101161, 69451 WEINHEIM, GERMANY
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
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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