Pd-catalyzed diastereoselective trifluoromethylthiolation of functionalized acrylamides

Qun Zhao (1) , Thomas Poisson (1) , Xavier Pannecoucke (1) , J.-P. Bouillon (1) , Tatiana Besset (1)

1 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse

The Pd-catalyzed diastereoselective trifluoromethylthiolation of acrylamides was developed to allow the formation of the Z-isomer as a single product. Using a C–H bond functionalization strategy, the method was applied to a broad range of α-aryl, α-alkyl, and α,β-disubstituted acrylamides bearing the amide derived from the 8-aminoquinoline as a directing group. Mechanistic studies as well as postfunctionalization of the products were performed. This approach opens new routes to unprecedented SCF3-containing scaffolds.

Domains: Chemical Sciences

Qun Zhao, Thomas Poisson, Xavier Pannecoucke, J.-P. Bouillon, Tatiana Besset. Pd-catalyzed diastereoselective trifluoromethylthiolation of functionalized acrylamides. Organic Letters, 2017, 19 (19), pp.5106-5109. ⟨10.1021/acs.orglett.7b02384⟩. ⟨hal-02046318⟩