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Cobalt-Catalyzed 2‑(1-Methylhydrazinyl)pyridine-Assisted C–H Alkylation/Annulation: Mechanistic Insights and Rapid Access to Cyclopenta[c]isoquinolinone Derivatives

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journal contribution
posted on 27.09.2021, 23:29 authored by Hongbin Zhai, Miao Liu, Chao Wang, Shuxian Qiu, Jian Wei, Hongjian Yang, Yundong Wu
We have developed cobalt-catalyzed, bidentate 2-(1-methylhydrazinyl)­pyridine (MHP)-directed C­(sp2)–H alkylation/annulation of benzoic hydrazides with various alkenes. Notably, diverse cyclopenta­[c]­isoquinolinones and dihydroisoquinolinones were obtained via this functional group-tolerant protocol. The reaction can be performed on a gram scale while maintaining an excellent yield, and the directing group can be removed efficiently under mild conditions. Furthermore, density-functional theory (DFT) calculations provide an incisive understanding of the observed regioselectivities for different olefins.