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Metal-free oxidative para-acylation of unprotected anilines with N-heteroarylmethanes

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Abstract

A selective oxidative para-acylation of unprotected anilines with methyl groups in N-heteroarylmethanes was achieved. This transformation proceeds under mild metal-free reaction conditions to produce the corresponding valuable diarylmethanones in good to high yields, featuring high site-selectivity, high functional-group-tolerance, gram-scale synthesis and easy product-derivation. Preliminary mechanistic studies revealed that the present oxidative para-acylation would take place via a Friedel–Crafts-type process of in situ imines and the steric hindrance might be the key issue for the high regio-selectivity.

Graphical abstract: Metal-free oxidative para-acylation of unprotected anilines with N-heteroarylmethanes

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Publication details

The article was received on 08 Oct 2017, accepted on 25 Oct 2017 and first published on 25 Oct 2017


Article type: Paper
DOI: 10.1039/C7OB02490H
Citation: Org. Biomol. Chem., 2017, Advance Article
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    Metal-free oxidative para-acylation of unprotected anilines with N-heteroarylmethanes

    M. Liu, X. Chen, T. Chen, Q. Xu and S. Yin, Org. Biomol. Chem., 2017, Advance Article , DOI: 10.1039/C7OB02490H

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