Issue 3, 2020

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

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

Supplementary files

Article information

Article type
Paper
Submitted
13 Oct 2019
Accepted
26 Nov 2019
First published
26 Nov 2019

Org. Biomol. Chem., 2020,18, 450-464

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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