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A Convergent Synthesis of Functionalized Alkenyl Halides through Cobalt(III)‐Catalyzed Three‐Component C−H Bond Addition
Author(s) -
Boerth Jeffrey A.,
Ellman Jonathan A.
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201705817
Subject(s) - chemistry , halide , aryl , catalysis , alkyl , medicinal chemistry , amide , cobalt , pyrazole , reactivity (psychology) , combinatorial chemistry , organic chemistry , medicine , alternative medicine , pathology
A Co III ‐catalyzed three‐component coupling of C(sp 2 )−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.