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Rh-catalyzed regio-switchable cross-coupling of gem-difluorinated cyclopropanes with allylboronates to structurally diverse fluorinated dienes† † Electronic supplementary information (ESI) available. See DOI: https://doi.org/10.1039/d2sc04118a

ABSTRACT: The control of linear/branched selectivity is one of the major focuses in transition-metal catalyzed allyl–allyl cross-coupling reactions, in which bond connection occurs at the terminal site of both the allyl fragments forming different types of 1,5-dienes. Herein, terminal/internal regioselectivity is investigated and found to be switchable in allyl–allyl cross-coupling reactions between gem-difluorinated cyclopropanes and allylboronates. The controlled terminal/internal regioselectivity arises from the fine-tuning of the rhodium catalytic system. Fluorinated 1,3-dienes, 1,4-dienes and 1,5-dienes are therefore produced in good yields with respectively isomerized terminal, internal, and terminal regioselectivity. Rh-catalyzed regio-switchable cross-coupling reactions of gem-difluorinated cyclopropanes with allylboronates have been developed. Fluorinated 1,4-dienes, 1,5-dienes and 1,3-dienes are produced in good yields with excellent regioselectivity.

SUBMITTER: Zeng Y

PROVIDER: S-EPMC9629036 | biostudies-literature | 2022 Oct

REPOSITORIES: biostudies-literature

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