Rh(III)-Catalyzed Diverse C-H Functionalization of Iminopyridinium Ylides

Main observation and conclusion Divergent synthesis of useful skeletons has been realized via rhodium(III)-catalyzed C-H activation of iminopyridinium ylides and coupling with various unsaturated coupling reagents. Isocoumarins and isoquinolones were obtained via cleavage of the C-N or N-N bond in the ylidic directing group, while fluorinated alkenes were delivered with the directing group intact. The reactions occurred with wide substrate scopes and good efficiency under redox-neutral and air-tolerant conditions. Representative products exhibit solid-state fluorescent property and bioactivity of inhibition toward human cancer cells.

Automated summary

Divergent synthesis of useful skeletons has been achieved through rhodium(III)-catalyzed C-H activation of iminopyridinium ylides and coupling with various unsaturated coupling reagents. The reactions yield isocoumarins, isoquinolones, and fluorinated alkenes with wide substrate scopes and good efficiency under redox-neutral and air-tolerant conditions. Representative products exhibit solid-state fluorescent property and bioactivity of inhibition toward human cancer cells.