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Issue 44, 2018
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Metal-free synthesis of aminomethylated imidazoheterocycles: dual role of tert-butyl hydroperoxide as both an oxidant and a methylene source

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Abstract

A novel and efficient aminomethylation approach has been developed for the regioselective functionalization of imidazoheterocycles under metal-free conditions. A wide range of imidazoheterocycles and 2/4-aminoazaheterocycles successfully provided corresponding aminomethylated imidazoheterocycles in moderate to excellent (33–80%) yields. The isotopic labelling study suggested that TBHP played a dual role as both an oxidant and a methylene source in this transformation. The developed protocol follows a radical pathway which is supported by radical trapping experiments.

Graphical abstract: Metal-free synthesis of aminomethylated imidazoheterocycles: dual role of tert-butyl hydroperoxide as both an oxidant and a methylene source

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Publication details

The article was received on 29 Sep 2018, accepted on 24 Oct 2018 and first published on 24 Oct 2018


Article type: Paper
DOI: 10.1039/C8OB02432D
Citation: Org. Biomol. Chem., 2018,16, 8620-8628
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    Metal-free synthesis of aminomethylated imidazoheterocycles: dual role of tert-butyl hydroperoxide as both an oxidant and a methylene source

    O. P. S. Patel, N. K. Nandwana, A. K. Sah and A. Kumar, Org. Biomol. Chem., 2018, 16, 8620
    DOI: 10.1039/C8OB02432D

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