Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 18, Issue 3, Pages 450-464Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c9ob02217a
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Funding
- National Research Foundation of Korea (NRF) - Ministry of Education, Science, and Technology [2017R1E1A1A01076642]
- Gachon University [GCU-2019-0328]
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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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