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The nucleophilic aromatic substitution (SNAr) between heteroaryl halides (Cl, Br) and thiols proceeds smoothly in DMAc under the action of K2CO3 at rt–100 °C. For most electron-deficient heteroarenes, reaction takes place without introducing an additional electron-withdrawing group. For electron-rich heteroarenes, an additional electron-withdrawing group such as a simple ester, keto, cyano, and nitro group is required to ensure the reaction completes.
The nucleophilic aromatic substitution (SNAr) between heteroaryl halides (Cl, Br) and thiols proceeds smoothly in DMAc under the action of K2CO3 at rt–100 °C. For most electron-deficient heteroarenes, reaction takes place without introducing an additional electron-withdrawing group. For electron-rich heteroarenes, an additional electron-withdrawing group such as a simple ester, keto, cyano, and nitro group is required to ensure the reaction completes.
Assembly of (Hetero)aryl Thioethers via Simple Nucleophilic Aromatic Substitution and Cu-Catalyzed Coupling Reaction with (Hetero)aryl Chlorides and Bromides under Mild Conditions The requirement of higher reaction temperatures for a SNAr reaction between thiols and less reactive electron-poor aryl halides in early reports has triggered intensive studies on the development of metal- and photo-catalyzed methods to promote this transformation.
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