Cobalt-Catalyzed Secondary Alkylation of Arenes and Olefins with Alkyl Ethers through the Cleavage of C(sp2)-H and C(sp3)-O Bonds

Xunqing Dong, Qun Li, Guigen Li, Hongjian Lu

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6 Scopus citations

Abstract

A novel cobalt-catalyzed C-H alkylation of arenes and olefins is achieved with (pyridin-2-yl)isopropyl amine as an N,N-bidentate directing group. Different linear, branched, and cyclic alkyl ethers were used as practical secondary alkylating reagents through cleavage of C(sp3)-O bond, providing an efficient approach to the synthesis of verstile o-alkylated arylamides and tetrasubstituted acrylamides. Mechanistic studies indicate that cleavage of the inert C(sp3)-O bond involves a cobalt-promoted radical process and that cleavage of the inert C(sp2)-H bond by a cobalt catalyst is a rate-limiting step.

Original languageEnglish
Pages (from-to)13402-13413
Number of pages12
JournalJournal of Organic Chemistry
Volume83
Issue number21
DOIs
StatePublished - Nov 2 2018

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