Organic Letters
Organic Letters
5 years ago

Metal-Free Sequential C(sp2)–H/OH and C(sp3)–H Aminations of Nitrosoarenes and N-Heterocycles to Ring-Fused Imidazoles

Metal-Free Sequential C(sp2)–H/OH and C(sp3)–H Aminations of Nitrosoarenes and N-Heterocycles to Ring-Fused Imidazoles
Hemant Kumar Srivastava, Subhra Kanti Roy, Chandan K. Jana, Anisha Purkait
Hydrogen bond assisted ortho-selective C(sp2)–H amination of nitrosoarenes and subsequent α-C(sp3)-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 (SNArH) was found to be preferred over classical SNAr reaction during the C(sp2)–H amination of halogenated nitrosoarenes.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b00832

DOI: 10.1021/acs.orglett.7b00832

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