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A Convergent Synthesis of Functionalized Alkenyl Halides through Cobalt(III)-Catalyzed Three-Component C-H Bond Addition.

ABSTRACT: A CoIII -catalyzed three-component coupling of C(sp2 )-H bonds, alkynes, and halogenating agents to give alkenyl halides is reported. This transformation proceeds with high regio- and diastereoselectivity, and is effective for a broad range of aryl and alkyl terminal alkynes. Diverse C-H bond partners also exhibit good reactivity for a range of heteroaryl and aryl systems as well as synthetically useful secondary and tertiary amide, urea, and pyrazole directing groups. This multicomponent transformation is also compatible with allenes in place of alkynes to furnish tetrasubstituted alkenyl halides, showcasing the first halo-arylation of allenes.

SUBMITTER: Boerth JA

PROVIDER: S-EPMC5568819 | biostudies-literature | 2017 Aug

REPOSITORIES: biostudies-literature

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A Convergent Synthesis of Functionalized Alkenyl Halides through Cobalt(III)-Catalyzed Three-Component C-H Bond Addition.

Boerth Jeffrey A JA Ellman Jonathan A JA

Angewandte Chemie (International ed. in English) 20170717 33

A Co<sup>III</sup> -catalyzed three-component coupling of C(sp<sup>2</sup> )-H bonds, alkynes, and halogenating agents to give alkenyl halides is reported. This transformation proceeds with high regio- and diastereoselectivity, and is effective for a broad range of aryl and alkyl terminal alkynes. Diverse C-H bond partners also exhibit good reactivity for a range of heteroaryl and aryl systems as well as synthetically useful secondary and tertiary amide, urea, and pyrazole directing groups. This ...[more]

PMID: 28657674

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