A 1,2-Aryl Migration Reaction in Visible-Light-Mediated Synthesis of Quinoxaline Derivatives: Mechanistic Studies
Tuan H. Ho, Binh Khanh, Tuong Anh To, Thành Vinh Nguyễn
Abstract
The synthesis of quinoxaline derivatives holds critical importance in various fields ranging from pharmaceuticals to material science. In this study, we introduce a practical light-mediated method for the efficient synthesis of quinoxaline derivatives. This approach enabled the sequential two-step, one-pot synthesis of 1,2-dihydro-2,2-diaryl-substituted quinoxalines from quinones, alkynes, and diamines. By adjusting the stoichiometric ratios and reaction conditions, the method was shifted to yield 2,3-diaryl-substituted quinoxalines exclusively, demonstrating remarkable versatility and efficiency. This switch in reaction outcomes was revealed to involve an oxidative 1,2-aryl migration through a combination of thorough experimental and computational mechanistic studies.