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Direct Arylations of Heteroarenes with Benzenesulfonyl Chlorides Using Pd/C Catalyst

Abstract : The reactivity of heteroaromatics in direct arylation with benzenesulfonyl chlorides using 10 % Pd/C as catalyst was explored. With (benzo)thiophenes, (benzo)furans, pyrroles and selenophenes, high yields in arylated heteroarenes were obtained. These arylations were performed using only 5 mol-% Pd/C and Li2CO3 as inexpensive base. The regioselectivities are similar to those observed with homogeneous palladium catalysts. Better yields were obtained with electron-deficient benzenesulfonyl chlorides than with the electron-rich ones. Notably, useful substituents such as bromo or iodo on the benzenesulfonyl chloride were tolerated, as no cleavage of the C-Br or C-I bonds was observed under these conditions. The use of Pd/C presents several advantages compared to the previously employed homogeneous palladium catalysts, as it can be easily removed by filtration at the end of the reaction. The major side-products of the reaction are HBr associated to Li2CO3. Therefore, this new protocol affords a very attractive synthetic scheme in terms of cost, simplicity and low environmental impact for the access to arylated heteroaromatics.
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Submitted on : Tuesday, January 19, 2021 - 9:02:08 AM
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Shuxin Mao, Xinzhe Shi, Jean-François Soulé, Henri Doucet. Direct Arylations of Heteroarenes with Benzenesulfonyl Chlorides Using Pd/C Catalyst. European Journal of Organic Chemistry, Wiley-VCH Verlag, 2020, 2020 (1), pp.91-97. ⟨10.1002/ejoc.201901561⟩. ⟨hal-02438552v2⟩

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