Trifluoromethylthiolation of α-Chloroaldehydes: Access to Quaternary SCF3-Containing Centers - Normandie Université Access content directly
Journal Articles European Journal of Organic Chemistry Year : 2018

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.
No file

Dates and versions

hal-02024498 , version 1 (19-02-2019)

Identifiers

Cite

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, 2018, Special Issue: Organofluorine Chemistry in Europe, 2018 (27-28), pp.3693-3696. ⟨10.1002/ejoc.201800418⟩. ⟨hal-02024498⟩
16 View
0 Download

Altmetric

Share

Gmail Mastodon Facebook X LinkedIn More