期刊
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2015, 期 20, 页码 4428-4436出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201500354
关键词
Homogeneous catalysis; Palladium; Cross-coupling; C-H bond activation; Arylation; Heteroarenes
资金
- French Ministere de la Recherche
- Centre National de la Recherche Scientifique (CNRS)
- Rennes Metropole
- Scientific Ministry of Higher Education and Research of Tunisia
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 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 tribromobenzenesulfonyl chlorides were successfully coupled with a range of heteroarenes without cleavage of the C-Br or C-I bonds and very regioselective arylations were observed in all cases. The reaction was also found to tolerate bromo substituents on the heteroarene.
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