Ir(III)-catalyzed quadruple C-H activation of N-arylimidazolium and diaryliodonium salts: facile access to polysubstituted imidazo[1,2- f]phenanthridiniums

Zheng Liu; Qian Li; Chengyong Yang; Xuesong Zheng; Di Wu; Ge Gao; Jingbo Lan

doi:10.1039/d2cc01646j

Ir(III)-catalyzed quadruple C-H activation of N-arylimidazolium and diaryliodonium salts: facile access to polysubstituted imidazo[1,2- f]phenanthridiniums

Chem Commun (Camb). 2022 Jun 21;58(50):7042-7045. doi: 10.1039/d2cc01646j.

Authors

Zheng Liu¹, Qian Li¹, Chengyong Yang¹, Xuesong Zheng¹, Di Wu¹, Ge Gao¹, Jingbo Lan¹

Affiliation

¹ Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, Sichuan University, 29 Wangjiang Road, Chengdu 610064, P. R. China. [email protected].

PMID: 35647666
DOI: 10.1039/d2cc01646j

Abstract

Herein, N-heterocyclic carbene-directed Ir(III)-catalyzed cascade C-H arylation/annulation of N-arylimidazolium with diaryliodonium salts has been accomplished for the first time via a quadruple C-H activation strategy to construct imidazo[1,2-f]phenanthridinium structures. This protocol overcomes the compatibility of three kinds of different C-H activations with high catalytic efficiency, which allows ortho-unhindered N-arylimidazoliums to undergo a diarylation/annulation reaction, affording a variety of polysubstituted imidazo[1,2-f]phenanthridiniums. Neutral imidazo[1,2-f]phenanthridines are also prepared via a demethylation reaction of imidazo[1,2-f]phenanthridiniums.