Citation: Peiyan Zhu, Yanyan Yang, Hui Li, Jinhua Wang, Shiqing Li. Rh(Ⅲ)‐Catalyzed sequential ring‐retentive/‐opening [4 + 2] annulations of 2H‐imidazoles towards full‐color emissive imidazo[5,1‐a]isoquinolinium salts and AIE‐active non‐symmetric 1,1′‐biisoquinolines[J]. Chinese Chemical Letters, ;2024, 35(10): 109533. doi: 10.1016/j.cclet.2024.109533 shu

Rh(Ⅲ)‐Catalyzed sequential ring‐retentive/‐opening [4 + 2] annulations of 2H‐imidazoles towards full‐color emissive imidazo[5,1‐a]isoquinolinium salts and AIE‐active non‐symmetric 1,1′‐biisoquinolines

Guangxi Key Laboratory of Electrochemical and Magneto-Chemical Functional Materials, College of Chemistry and Bioengineering, Guilin University of Technology, Guilin 541004, China

lisq@glut.edu.cn

Received Date: 12 October 2023
Revised Date: 8 January 2024
Accepted Date: 15 January 2024
Available Online: 22 January 2024

Figures(7)

Rhodium-catalyzed C4_aryl−H activation and ring-retentive annulation of 2H-imidazoles with internal alkynes to build imidazo[5,1-a]isoquinolinium salts with high yields and broad scope has been disclosed. These novel salts serve as new full-color emissive fluorophores (433−633 nm), just by simply modifying the substituents on C3 and C4 positions of isoquinoline ring. Furthermore, these salts can undergo ring-opening C5_aryl−H activation/annulation with a different alkyne to form non-symmetric and AIE-active 1,1′-biisoquinolines, where NH₄OAc plays an indispensable role that accounts for Hofmann elimination and imine formation, leading to an unprecedented imine dance: cyclic imine → N-alkenyl imine → NH imine. The ¹⁵N labelling experiments indicate that the 2^nd annulation includes two pathways: N-exchange (major) and N-retention (minor).
- C-H activation/annulation,
- 2H-Imidazole,
- Imidazo[5,1-a]isoquinolinium,
- 1,1′-Biisoquinolines,
- Full-color emission,
- Ring-retentive/-opening
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