Tandem Carbon Carbon Bond Forming Reaction via Zincate Carbenid

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The electrophilic character of carbenoids as a-metallated carbocation equivalents has not been fully demonstrated in contrast to their widely studied nucleophilic nature. In the present study, we disclosed that lithium(1bromoalkenyl)(dialkyl)zincate and lithium(1-bromocyclopropyl)(dialkyl)-zincate which can be generated by a Br/Zn exchange reaction of the corresponding gem-dibromo compounds undergo a facile intramolecular alkylation reaction to give alkenyl- and cyclopropylzinc species. Since the resulting organozinc intermediates have potential of undergoing further C-C bond formation, the reaction was extended to the tandem substitution reaction of gem-dibromo compounds via Pd(O)catalyzed arylation, acylation and alkenylation reaction.