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Rhodium(III)-Catalyzed Redox-Neutral Synthesis of Isoquinolinium Salts via C-H Activation of Imines

Miaomiao Tian, Guangfan Zheng, Xuesen Fan and Xingwei Li*

*Henan Key Laboratory of Organic Functional Molecule and Drug Innovation, Henan Normal University, Xinxiang 453007, China, Email: xwlidicp.ac.cn

M. Tian, G. Zheng, X. Fan, X. Li, J. Org. Chem., 2018, 83, 6477-6488.

DOI: 10.1021/acs.joc.8b00758 (free Supporting Information)


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Abstract

A zinc salt promotes cyclization as well as provides a counteranion in a redox-neutral synthesis of isoquinolinium salts via C-H activation of presynthesized or in situ formed imines and coupling with α-diazo ketoesters. Under three-component conditions, both ketone and aldehydes are viable substrates. The coupling of imines with diazo malonates under similar conditions afforded isoquinolin-3-ones as the coupling product.

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Key Words

isoquinolinium salts, multicomponent reactions


ID: J42-Y2018