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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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Publication details

The article was received on 13 Oct 2019, accepted on 26 Nov 2019 and first published on 26 Nov 2019


Article type: Paper
DOI: 10.1039/C9OB02217A
Org. Biomol. Chem., 2020, Advance Article

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    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, Advance Article , DOI: 10.1039/C9OB02217A

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