912762-95-9Relevant articles and documents
Direct Arylations of Heteroarenes with Benzenesulfonyl Chlorides Using Pd/C Catalyst
Mao, Shuxin,Shi, Xinzhe,Soulé, Jean-Fran?ois,Doucet, Henri
, p. 91 - 97 (2019/12/30)
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.
Visible-light photocatalyzed synthesis of 2-aryl N-methylpyrroles, furans and thiophenes utilizing arylsulfonyl chlorides as a coupling partner
Natarajan, Palani,Bala, Anu,Mehta,Bhasin
, p. 2521 - 2526 (2016/04/26)
Visible-light (Blue LED lamp: hν=425±15 nm) photocatalyzed cross-coupling reactions of arylsulfonyl chloride with N-methylpyrrole, furan, thiophene and their derivatives have been achieved in moderate to good yields at room temperature. A plausible mechan
Pd-Catalysed Direct Arylation of Heteroaromatics Using (Poly)halobenzenesulfonyl Chlorides as Coupling Partners: One Step Access to (Poly)halo-Substituted Bi(hetero)aryls
Skhiri, Aymen,Beladhria, Anissa,Yuan, Kedong,Soulé, Jean-Francois,Ben Salem, Ridha,Doucet, Henri
, p. 4428 - 4436 (2015/07/27)
The reactivity of (poly)halo-substituted benzenesulfonyl chlorides for Pd-catalysed desulfitative arylation was investigated. 2-, 3- and 4-bromobenzenesulfonyl chlorides react nicely to afford arylated heteroarenes in moderate to high yields without cleav