Visible-Light-Driven [3+2]/[4+2] Annulation Reactions of Alkenes with N-Aminopyridinium Salts

The annulation reactions of benzoamidyl radicals with alkenes were realized under visible light irradiation with fac-Ir(ppy)(3) as catalyst and N-aminopyridinium salts as benzoamidyl radical precursors. The reaction can deliver two distinct types of products: in the case of vinyl arenes, [3 + 2] annulation product dihydrooxazoles were yielded exclusively; when alkyl-substituted alkenes were used, on the other hand, it afforded [4 + 2] annulation product dihydroisoquinolinones. Factors determining the reaction consequence were elucidated by DFT calculations.

Automated summary

The annulation reactions of benzoamidyl radicals with alkenes under visible light irradiation using fac-Ir(ppy)(3) as a catalyst and N-aminopyridinium salts as precursors yielded different products depending on the structure of the alkene. Factors influencing the reaction outcome were elucidated by DFT calculations.