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Cooperative NHC/Photoredox Catalyzed Ring-Opening of Aryl Cyclopropanes to 1-Aroyloxylated-3-Acylated Alkanes.

ABSTRACT: Cyclopropanes are an important class of building blocks in organic synthesis. Herein, a ring-opening/arylcarboxylation/acylation cascade reaction for the 1,3-difunctionalization of aryl cyclopropanes enabled by cooperative NHC and organophotoredox catalysis is reported. The cascade works on monosubstituted cyclopropanes that are in contrast to the heavily investigated donor-acceptor cyclopropanes more challenging to be difunctionalized. The key step is a radical/radical cross coupling of a benzylic radical generated in the photoredox catalysis cycle with a ketyl radical from the NHC catalysis cycle. The transformation features metal-free reaction conditions and tolerates a diverse range of functionalities.

SUBMITTER: Zuo Z

PROVIDER: S-EPMC9298441 | biostudies-literature | 2021 Nov

REPOSITORIES: biostudies-literature

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Cooperative NHC/Photoredox Catalyzed Ring-Opening of Aryl Cyclopropanes to 1-Aroyloxylated-3-Acylated Alkanes.

Zuo Zhijun Z Daniliuc Constantin G CG Studer Armido A

Angewandte Chemie (International ed. in English) 20211025 48

Cyclopropanes are an important class of building blocks in organic synthesis. Herein, a ring-opening/arylcarboxylation/acylation cascade reaction for the 1,3-difunctionalization of aryl cyclopropanes enabled by cooperative NHC and organophotoredox catalysis is reported. The cascade works on monosubstituted cyclopropanes that are in contrast to the heavily investigated donor-acceptor cyclopropanes more challenging to be difunctionalized. The key step is a radical/radical cross coupling of a benzy ...[more]

PMID: 34580972

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