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Pd-Catalyzed Trifluoromethylthiolation of Unsaturated Compounds: A General Approach

Abstract : A Pd‐catalyzed directed trifluoromethylthiolation of acrylamides and aromatic amides by C–H bond functionalization was developed by using the Munavalli reagent in the absence of additives. This general approach allowed the direct introduction of the SCF3 group on unsaturated amides in moderate to good yields and offered a straightforward access to various original SCF3‐containing molecules. In this study, a general approach towards the synthesis of trifluoromethylthiolated olefinic and aromatic compounds was developed. Under Pd‐catalysis, the direct introduction of a SCF3 group was realized in the presence of the Munavalli reagent as the electrophilic SCF3 source and in the absence of additives. A large number of acrylamides and aromatic amides derived from 8‐aminoquinoline and 5‐methoxy‐aminoquinoline were functionalized in moderate to high yields (up to 89 %). The cleavage of the directing groups was smoothly achieved, demonstrating further the synthetic utility of the present approach and offering a straightforward access to various original SCF3‐containing molecules.
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https://hal-normandie-univ.archives-ouvertes.fr/hal-02024539
Contributor : Madeleine Roux-Merlin <>
Submitted on : Tuesday, February 19, 2019 - 11:11:14 AM
Last modification on : Wednesday, July 15, 2020 - 2:44:10 PM

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Qun Zhao, Mu-Yi Chen, Thomas Poisson, Xavier Pannecoucke, J.-P. Bouillon, et al.. Pd-Catalyzed Trifluoromethylthiolation of Unsaturated Compounds: A General Approach. European Journal of Organic Chemistry, Wiley-VCH Verlag, 2018, Special Issue: C‐H Activation in Organic Synthesis, 2018 (44), pp.6167-6175. ⟨10.1002/ejoc.201801071⟩. ⟨hal-02024539⟩

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