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Pd-catalyzed diastereoselective trifluoromethylthiolation of functionalized acrylamides

Abstract : 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.
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https://hal-normandie-univ.archives-ouvertes.fr/hal-02046318
Contributor : Madeleine Roux-Merlin <>
Submitted on : Friday, February 22, 2019 - 3:40:31 PM
Last modification on : Monday, July 27, 2020 - 3:16:56 PM

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

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