Pd-Catalysed Direct Arylation of Heteroaromatics Using (Poly)halobenzene-sulfonyl Chlorides as Coupling Partners: One Step Access to (Poly)halo-Substituted Bi(hetero)aryls - Université de Rennes Accéder directement au contenu
Article Dans Une Revue European Journal of Organic Chemistry Année : 2015

Pd-Catalysed Direct Arylation of Heteroaromatics Using (Poly)halobenzene-sulfonyl Chlorides as Coupling Partners: One Step Access to (Poly)halo-Substituted Bi(hetero)aryls

Résumé

The reactivity of (poly)halo-substituted benzenesulfonyl chlorides for Pd-catalyzed desulfitative arylation was investigated. 2-, 3- and 4-bromobenzenesulfonyl chlorides react nicely to afford arylated heteroarenes in moderate to high yields without cleavage of the C-Br bonds, allowing further transformations. A minor influence upon reaction yeilds was found to be exerted by the bromo substituent on the benzene ring. Even 4-iodobenzenesulfonyl chloride, di- and tri-bromobenzenesulfonyl chlorides were successfully coupled with a range of heteroarenes without cleavage of the C-Br or C-I bonds and very regioselective arylations were obsd. in all cases. The reaction was also found to tolerate bromo substituents on the heteroarene.

Domaines

Chimie

Dates et versions

hal-01163648 , version 1 (15-06-2015)

Identifiants

Citer

Aymen Skhiri, Anissa Beladhria, Kedong Yuan, Jean-François Soulé, Ridha Ben Salem, et al.. Pd-Catalysed Direct Arylation of Heteroaromatics Using (Poly)halobenzene-sulfonyl Chlorides as Coupling Partners: One Step Access to (Poly)halo-Substituted Bi(hetero)aryls. European Journal of Organic Chemistry, 2015, 2015 (20), pp.4428-4436. ⟨10.1002/ejoc.201500354⟩. ⟨hal-01163648⟩
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