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Metal-Free Sequential C(sp(2))-H/OH and C(sp(3))-H Aminations of Nitrosoarenes and N-Heterocycles to Ring-Fused Imidazoles.

ABSTRACT

Hydrogen bond assisted ortho-selective C(sp(2))-H amination of nitrosoarenes and subsequent α-C(sp(3))-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(sp(2))-H amination of halogenated nitrosoarenes.