Visible-Light-Driven [3 + 2]/[4 + 2] Annulation Reactions of Alkenes with<i>N</i>-Aminopyridinium Salts
Yu‐Zhao Wang, Peng‐Yu Liang, Hongchao Liu, Wu‐Jie Lin, Panpan Zhou, Wei Yu
Abstract
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.
Topics & Concepts
AnnulationChemistryRadicalCatalysisPhotochemistryAlkylVisible spectrumMedicinal chemistryOrganic chemistryOptoelectronicsPhysicsCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsOxidative Organic Chemistry Reactions