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Photoredox-catalyzed cyclopropanation of allenes towards vinyl-cyclopropanes.


ABSTRACT: While the vinyl cyclopropane (VCP) scaffold exhibits unique reactivity in chemical transformations, its synthesis presents certain challenges. Herein, we report the visible-light photoredox-catalyzed radical-polar crossover cyclization (RPCC) of terminal and internal allenes with carboxylic acids, realizing the construction of functionalized vinyl cyclopropanes (VCPs) with highly chemo-, and regioselectivities under mild conditions. Moreover, this photoredox protocol exhibits good functional group tolerance, a broad substrate scope, facile scalability and easy rearrangement to give various cyclopentene units.

SUBMITTER: Xie H 

PROVIDER: S-EPMC12366832 | biostudies-literature | 2025 Sep

REPOSITORIES: biostudies-literature

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Photoredox-catalyzed cyclopropanation of allenes towards vinyl-cyclopropanes.

Xie Hui H   Zhang Yan Y   Breit Bernhard B  

Chemical science 20250814 36


While the vinyl cyclopropane (VCP) scaffold exhibits unique reactivity in chemical transformations, its synthesis presents certain challenges. Herein, we report the visible-light photoredox-catalyzed radical-polar crossover cyclization (RPCC) of terminal and internal allenes with carboxylic acids, realizing the construction of functionalized vinyl cyclopropanes (VCPs) with highly chemo-, and regioselectivities under mild conditions. Moreover, this photoredox protocol exhibits good functional gro  ...[more]

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