Metal-free late-stage C(sp(2))-H functionalization of N-aryl amines with various sodium salts
- Authors
- Mudithanapelli, Chandrashekar; Kim, Mi-hyun
- Issue Date
- Jan-2020
- Publisher
- ROYAL SOC CHEMISTRY
- Citation
- ORGANIC & BIOMOLECULAR CHEMISTRY, v.18, no.3, pp.450 - 464
- Journal Title
- ORGANIC & BIOMOLECULAR CHEMISTRY
- Volume
- 18
- Number
- 3
- Start Page
- 450
- End Page
- 464
- URI
- https://scholarworks.bwise.kr/gachon/handle/2020.sw.gachon/17625
- DOI
- 10.1039/c9ob02217a
- ISSN
- 1477-0520
- Abstract
- Metal-free consecutive C(sp(2))-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(sp(2))-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.
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