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http://dx.doi.org/10.5012/bkcs.2005.26.9.1410

Nickel-Catalyzed Coupling of Arenesulfonates with Primary Alkylmagnesium Halides  

Cho, Chul-Hee (School of Chemical & Materials Engineering, Chung-Ang University)
Sun, Myung-Chul (School of Chemical & Materials Engineering, Chung-Ang University)
Park, Kwang-Yong (School of Chemical & Materials Engineering, Chung-Ang University)
Publication Information
Bulletin of the Korean Chemical Society / v.26, no.9, 2005 , pp. 1410-1414 More about this Journal
Abstract
Neopentyl arenesulfonates reacted with primary alkylmagnesium halides in the presence of $(PPh_3)_2NiCl_2$ to produce the corresponding alkylarenes. The efficiency of this coupling reaction considerably depends on the nature of catalyst and solvent. Highest yield was obtained by using three equivalents of Grignard reagent to a mixture of $(PPh_3)_2NiCl_2$ and arenesulfonate in refluxing $Et_2O$. This reaction represents a novel method allowing the efficient and creative substitution of sulfur-containing groups in aromatic compounds. It also shows that the alkyloxysulfonyl group might be a suitable alternative to halides and triflate in some circumstances.
Keywords
Primary alkyl Grignard reagents; Arenesulfonates; Cross-coupling; Nickel catalyst;
Citations & Related Records
Times Cited By KSCI : 1  (Citation Analysis)
Times Cited By Web Of Science : 6  (Related Records In Web of Science)
Times Cited By SCOPUS : 6
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