Organozinc pivalates for modular Cobalt-Catalyzed carbosulfonylation of 1,3-Enynes

Salt-stabilized organozinc pivalates display crucial counterion-effect by OPiv-coordination, which steer an efficient cobalt-catalyzed 1,4-carbosulfonylation of 1,3-enynes with sulfonyl chlorides under simple and mild reaction conditions. Notably, both aryl and alkyl zinc pivalates show superior reactivity com-pared to conventional halide-supported organozinc reagents, thus providing an expedient access to the preparation of highly functionalized a-allenyl sulfones via cascade C-C/C-S bond formation. Moreover, late-stage modifications of drug-like compounds and facile transformations of the resulting allenes illus-trate the synthetic utility of this protocol.& COPY; 2023 Elsevier Inc. All rights reserved.

Automated summary

Salt-stabilized organozinc pivalates with OPiv-coordination exhibit significant counterion-effect, enabling an efficient cobalt-catalyzed 1,4-carbosulfonylation of 1,3-enynes with sulfonyl chlorides under mild conditions. Both aryl and alkyl zinc pivalates show higher reactivity compared to traditional halide-supported organozinc reagents, providing a convenient access to highly functionalized a-allenyl sulfones through cascade C-C/C-S bond formation. Additionally, late-stage modifications of drug-like compounds and facile transformations of the resulting allenes demonstrate the synthetic utility of this protocol.