Cobalt-Catalyzed 2‑(1-Methylhydrazinyl)pyridine-Assisted C–H Alkylation/Annulation: Mechanistic Insights and Rapid Access to Cyclopenta[c]isoquinolinone Derivatives
journal contributionposted on 27.09.2021, 23:29 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.
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>] isoquinolinone derivativesdiverse cyclopenta [<methylhydrazinyl ) pyridinecyclopenta [<various alkenestolerant protocolsp </removed efficientlyrapid accessobtained viaobserved regioselectivitiesmild conditionsmechanistic insightsincisive understandinggram scalefunctional theoryfunctional groupexcellent yielddirecting groupdifferent olefinscalculations providec </benzoic hydrazides>] isoquinolinones>< sup