A simple, efficient and green methodology for the C−S cross‐coupling reaction using Pd(L‐Pro)2 as a heterogeneous catalyst was developed involving aryl iodides, thiols, green‐solvent and a low catalytic loading of palladium prolinate. In addition, the catalyst turned out to be recyclable and the products were obtained in good to excellent yields.
Functionalization of 2,1,3‐benzothiadiazole (BTD) with thiols at C‐5 position remains low explored. Moreover, the arylthiol‐substitutions at this position are also unexplored and can not be found by a SN2 or SN1 reaction. In this sense, herein we present a new palladium‐catalyzed methodology for a wide variety of unpublished 5‐arylsulfanyl‐benzo‐2,1,3‐thiadiazole derivatives synthesis with moderate to high yields using a low catalytic loading of Pd(L‐Pro)2 as low‐coast, and efficient catalyst in low reaction time. Besides, we concluded that the pKa of thiol species has an important role in this catalysis, mainly in the CMD like catalytic cyclo process, which strongly interferes in the reaction yields. Furthermore, arylsulfanyl‐benzo‐2,1,3‐thiadiazoles derivatives have been assessed (in vitro) as potential acetylcholinesterase inhibitors.
[Ce(l-Pro)2]2 (Oxa) was used as a recyclable heterogeneous catalyst under mild conditions for the preparation of 2-aryl-2,3-dihydroquinazolin-4(1H)-one derivatives. The one-pot protocol proceeds in ethanol using anthranilamide with several aldehydes at 50–55 °C. The catalyst can be recycled and reused three cycles without significant loss of catalytic activity.
A simple, efficient and green chemical ultrasound assisted thio-Michael addition reaction between thiols and (Z)-azlactones aiming non-natural amino acid derivatives using chiral Zn[(l)-Pro]2as a heterogeneous catalyst is herein described.
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