Department of Chemistry, Indian Institute of Technology Guwahati , Guwahati, India 781039.
Org Lett. 2017 May 19;19(10):2540-2543. doi: 10.1021/acs.orglett.7b00832. Epub 2017 May 9.
Hydrogen bond assisted ortho-selective C(sp)-H amination of nitrosoarenes and subsequent α-C(sp)-H functionalization of aliphatic amines is achieved under metal-free conditions. The annulation of nitrosoarenes and 2-hydroxy-C-nitroso compounds with N-heterocycles provides a facile excess to a wide range of biologically relevant ring-fused benzimidazoles and structurally novel polycyclic imidazoles, respectively. Nucleophilic aromatic hydrogen substitution (SArH) was found to be preferred over classical SAr reaction during the C(sp)-H amination of halogenated nitrosoarenes.
在无金属条件下，实现了硝基芳族化合物和随后的脂肪族胺的 C(sp)-H 邻位选择性氨化以及随后的α-C(sp)-H 官能化。通过氮杂环与 2-羟基-C-亚硝基化合物的环化反应，分别为一系列广泛的具有生物学相关性的环合苯并咪唑和结构新颖的多环咪唑提供了简便的途径。在卤代硝基芳族化合物的 C(sp)-H 氨化过程中，发现亲核芳香氢取代（SArH）优先于经典的 SAr 反应。
