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Issue 3, 2020
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Metal-free late-stage C(sp2)–H functionalization of N-aryl amines with various sodium salts

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Abstract

Metal-free consecutive C(sp2)–X (X = Cl, Br, S, N) bond formations of N-aryl amines (cyclic, fused, carbamate, and aminium radicals) were achieved under mild conditions using [bis(trifluoroacetoxy)iodo]benzene (PIFA) and simple nonharmful sodium salts. This direct and selective C(sp2)–H functionalization showed excellent functional group compatibility, cost effectiveness, and late-stage applicability for the synthesis of biologically active natural products. Two mechanisms were proposed to explain the ortho- or para-preference, as well as the accelerating effect of CH3NO2.

Graphical abstract: Metal-free late-stage C(sp2)–H functionalization of N-aryl amines with various sodium salts

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Supplementary files

Article information


Submitted
13 Oct 2019
Accepted
26 Nov 2019
First published
26 Nov 2019

Org. Biomol. Chem., 2020,18, 450-464
Article type
Paper

Metal-free late-stage C(sp2)–H functionalization of N-aryl amines with various sodium salts

C. Mudithanapelli and M. Kim, Org. Biomol. Chem., 2020, 18, 450
DOI: 10.1039/C9OB02217A

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