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Ketone-catalyzed photochemical C(sp3)-H chlorination.

ABSTRACT: Photoexcited arylketones catalyze the direct chlorination of C(sp3)-H groups by N-chlorosuccinimide. Acetophenone is the most effective catalyst for functionalization of unactivated C-H groups while benzophenone provides better yields for benzylic C-H functionalization. Activation of both acetophenone and benzophenone can be achieved by irradiation with a household compact fluorescent lamp. This light-dependent reaction provides a better control of the reaction as compared to the traditional chlorination methods that proceed through a free radical chain propagation mechanism.

SUBMITTER: Han L

PROVIDER: S-EPMC5510956 | biostudies-literature | 2017 Jun

REPOSITORIES: biostudies-literature

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Ketone-catalyzed photochemical C(sp3)-H chlorination.

Han Lei L Xia Jibao J You Lin L Chen Chuo C

Tetrahedron 20170504 26

Photoexcited arylketones catalyze the direct chlorination of C(sp3)-H groups by N-chlorosuccinimide. Acetophenone is the most effective catalyst for functionalization of unactivated C-H groups while benzophenone provides better yields for benzylic C-H functionalization. Activation of both acetophenone and benzophenone can be achieved by irradiation with a household compact fluorescent lamp. This light-dependent reaction provides a better control of the reaction as compared to t ...[more]

PMID: 28717256

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