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Angew Chem Int Ed Engl. 2017 Aug 7;56(33):9976-9980. doi: 10.1002/anie.201705817. Epub 2017 Jul 17.

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

Author information

1
Department of Chemistry, Yale University, 225 Prospect St., New Haven, CT, 06520, USA.

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.

KEYWORDS:

C−H activation; alkynes; allenes; homogeneous catalysis; multicomponent reactions

PMID:
28657674
PMCID:
PMC5568819
DOI:
10.1002/anie.201705817
[Indexed for MEDLINE]
Free PMC Article

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