Two-Fold C-H/C-H Cross-Coupling Using RhCl3 ·3H2 O as the Catalyst: Direct Fusion of N-(Hetero)arylimidazolium Salts and (Hetero)arenes

Journal of the American Chemical Society
Zhijie SheJingsong You

Abstract

[Cp*RhCl2]2 is the most prevailing catalyst employed for rhodium-catalyzed chelation-assisted C-H/C-H cross-coupling reactions due to the special ligand effect of Cp*. In this article, a novel concept of using a simple inorganic rhodium salt, RhCl3·3H2O, as the catalyst by taking advantage of in situ π-coordination to Rh with a (hetero)aromatic reaction component to stabilize Rh intermediates is proposed and evaluated. Our studies not only prove the feasibility of this concept but also disclose a novel 2-fold C-H/C-H cross-coupling reaction of N-(hetero)arylimidazolium salts with various (hetero)arenes to access water-soluble, fluorescent, cationic, and planar polycyclic heteroaromatic molecules, in which RhCl3·3H2O outperforms [Cp*RhCl2]2. Mechanistic experiments and DFT calculations reveal that this successive quadruple C-H activation reaction consists of two different C-H activation modes, i.e., concerted metalation-deprotonation (CMD) and oxidative addition. Notably, this is the first report of a C-H bond activation via oxidative addition to RhI in a bi(hetero)aryl formation with hydrogen evolution. Finally, the different ligand electrochemical parameters of neutral (hetero)arenes and anionic Cp* are used to explain the dif...Continue Reading

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Citations

May 24, 2019·Chemical Communications : Chem Comm·Pirudhan KarakJoyanta Choudhury
Aug 20, 2019·Chemical Communications : Chem Comm·Zhigang WangGe Gao
Oct 29, 2020·Organic & Biomolecular Chemistry·Yu YuShiqing Li
Jul 22, 2021·Chemical Communications : Chem Comm·Hairong LyuZuowei Xie
Jan 23, 2020·Chemical Reviews·Qun ZhaoMichal Szostak
Jul 16, 2019·Journal of the American Chemical Society·Yik Ki AuZuowei Xie
Feb 15, 2019·Journal of the American Chemical Society·Jinwoo KimSukbok Chang
Nov 20, 2021·Chemical Reviews·Christian A MalapitShelley D Minteer
Feb 4, 2022·Chemical Communications : Chem Comm·Tianbao WangGe Gao

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