Nickel-catalyzed coupling of arenesulfonates with primary alkylmagnesium halides

초록

Neopentyl arenesulfonates reacted with primary alkylmagnesium halides in the presence of (PPh3)(2)NiCl2 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)(2)NiCl2 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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