Synthesis of 1,2-Fused/Disubstituted Benzimidazoles and Benzimidazolium Salts by I<sub>2</sub>-Mediated sp<sup>3</sup> C–H Amination
Xiaofei Yi, Zongxiang Zhao, Manman Wang, Wenquan Yu, Junbiao Chang
Abstract
An intramolecular sp3 C–H amination reaction of aniline derivatives has been established. This reaction employs molecular iodine (I2) under transition-metal-free conditions and produces 1,2-fused or 1,2-disubstituted benzimidazoles. This operationally simple synthetic process works well with N-substituted aniline substrates, forming novel benzimidazolium frameworks. Under the optimal reaction conditions, a broad variety of 1,2-fused/disubstituted benzimidazoles and benzimidazolium salts, including several bioactive compounds, were synthesized from readily accessible precursors in an efficient and scalable fashion.
Topics & Concepts
ChemistryAminationAnilineIntramolecular forceCombinatorial chemistryIodineTransition metalReaction conditionsOrganic chemistryCatalysisSynthesis and Catalytic ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques