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

Abstract : In this study, a straightforward methodology was developed to access quaternary α‐trifluoromethylthiolated chloroaldehydes. Using the Munavalli reagent as the electrophilic SCF3 source, a base‐catalyzed trifluoromethylthiolation reaction with a panel of α‐chloroaldehydes was successfully achieved under mild reaction conditions. The α‐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.
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Fabien Gelat, Thomas Poisson, A.T. Biju, Xavier Pannecoucke, Tatiana Besset. Trifluoromethylthiolation of α-Chloroaldehydes: Access to Quaternary SCF3-Containing Centers. European Journal of Organic Chemistry, Wiley-VCH Verlag, 2018, Special Issue: Organofluorine Chemistry in Europe, 2018 (27-28), pp.3693-3696. ⟨10.1002/ejoc.201800418⟩. ⟨hal-02024498⟩



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