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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 26, Number 9
BKCSDE 26(9)
September 20, 2005 

Nickel-Catalyzed Coupling of Arenesulfonates with Primary Alkylmagnesium Halides
Chul-Hee Cho, Myungchul Sun, Kwangyong Park*
Primary alkyl Grignard reagents, Arenesulfonates, Cross-coupling, Nickel catalyst
Neopentyl arenesulfonates reacted with primary alkylmagnesium halides in the presence of (PPh3)2NiCl2 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 (PPh3)2NiCl2 and arenesulfonate in refluxing Et2O. 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.
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