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Issue 1, 2020
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Base-promoted aerobic oxidation of N-alkyl iminium salts derived from isoquinolines and related heterocycles

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Abstract

Potassium tert-butoxide-promoted aerobic oxidation of N-alkyl iminium salts is reported. The reaction is atom-economical and environmentally friendly. Iminium salts derived from isoquinoline, quinoline, phenanthridine, phenanthroline, and phthalazine were successfully transformed into their corresponding unsaturated lactams with up to 95% yield under mild conditions in the absence of photocatalysts and metallic or organic catalysts. Owing to the general substrate scope, low cost, feasibility of scale up, wide availability of reagents, and green reaction conditions, this method shows great potential for preparing isoquinolones and related compounds. The method was applied for atom- and step-economical total synthesis of natural products such as norketoyobyrine.

Graphical abstract: Base-promoted aerobic oxidation of N-alkyl iminium salts derived from isoquinolines and related heterocycles

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Article information


Submitted
22 Oct 2019
Accepted
28 Nov 2019
First published
28 Nov 2019

Green Chem., 2020,22, 197-203
Article type
Paper

Base-promoted aerobic oxidation of N-alkyl iminium salts derived from isoquinolines and related heterocycles

L. Bai, Y. Zhou, X. Zhuang, L. Zhang, J. Xue, X. Lin, T. Cai and Q. Luo, Green Chem., 2020, 22, 197
DOI: 10.1039/C9GC03629F

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