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

We have developed cobalt-catalyzed, bidentate 2-(1-methylhydrazinyl)pyridine (MHP)-directed C(sp(2))-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.

Automated summary

A novel cobalt-catalyzed reaction has been successfully developed for the annulation of benzoic hydrazides with various alkenes, leading to diverse products; the reaction is suitable for large-scale preparation and efficient removal of the directing group under mild conditions; density-functional theory calculations provide a deeper understanding of the selectivity of different alkenes.