Gachon Institute of Pharmaceutical Science & Department of Pharmacy, College of Pharmacy, Gachon University, 191 Hambakmoeiro, Yeonsu-gu, Incheon 21936, Republic of Korea.
Org Biomol Chem. 2020 Jan 22;18(3):450-464. doi: 10.1039/c9ob02217a.
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.
使用[双(三氟乙酰氧基)碘]苯（PIFA）和简单无害的钠盐，在温和条件下实现了 N-芳基胺（环状、稠合、氨基甲酸酯和铵自由基）的无金属连续 C(sp2)-X（X = Cl、Br、S、N）键形成。这种直接和选择性的 C(sp2)-H 官能化反应表现出优异的官能团兼容性、成本效益和对生物活性天然产物合成的后期适用性。提出了两种机制来解释邻位或对位偏好以及 CH3NO2 的加速效应。
