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

Abstract : 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.
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https://hal-univ-rennes1.archives-ouvertes.fr/hal-01163648
Contributor : Laurent Jonchère <>
Submitted on : Monday, June 15, 2015 - 11:22:15 AM
Last modification on : Thursday, March 5, 2020 - 2:02:25 PM

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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, Wiley-VCH Verlag, 2015, 2015 (20), pp.4428-4436. ⟨10.1002/ejoc.201500354⟩. ⟨hal-01163648⟩

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