40949-56-2Relevant articles and documents
Visible-Light-Induced Remote C(sp3)-H Pyridylation of Sulfonamides and Carboxamides
Kim, Namhoon,Lee, Changseok,Kim, Taehwan,Hong, Sungwoo
, p. 9719 - 9723 (2019)
Visible-light-induced site-selective C(sp3)-H pyridylation of amides has been accomplished using N-amidopyridinium salts. The N-centered radicals generated by the single-electron reduction of N-amidopyridinium substrates undergo 1,5-hydrogen at
Micellar Catalysis: Visible-Light Mediated Imidazo[1,2-a]pyridine C—H Amination with N-Aminopyridinium Salt Accelerated by Surfactant in Water
Yang, Zhonglie,Cao, Kun,Peng, Xiaoyan,Lin, Li,Fan, Danchen,Li, Jun-Long,Wang, Jingxia,Zhang, Xiaobin,Jiang, Hezhong,Li, Jiahong
supporting information, p. 3347 - 3352 (2021/10/20)
A light-promoted metal-free protocol for the amination of imidazo[1,2-a]pyridines with N-aminopyridinium salt by the assistance of surfactants in water was reported, charactering mild and environmentally benign conditions, as well as great functional grou
Visible-Light-Enabled Ortho-Selective Aminopyridylation of Alkenes with N-Aminopyridinium Ylides
Moon, Yonghoon,Lee, Wooseok,Hong, Sungwoo
supporting information, p. 12420 - 12429 (2020/07/24)
By utilizing an underexplored reactivity mode of N-aminopyridinium ylides, we developed the visible-light-induced ortho-selective aminopyridylation of alkenes via radical-mediated 1,3-dipolar cycloaddition. The photocatalyzed single-electron oxidation of N-aminopyridinium ylides generates the corresponding radical cations that enable previously inaccessible 1,3-cycloaddition with a broader range of alkene substrates. The resulting cycloaddition adducts rapidly undergo subsequent homolytic cleavage of the N-N bond, conferring a substantial thermodynamic driving force to yield various β-aminoethylpyridines. Remarkably, amino and pyridyl groups can be installed into both activated and unactivated alkenes with modular control of ortho-selectivity and 1,2-syn-diastereoselectivity under metal-free and mild conditions. Combined experimental and computational studies are conducted to clarify the detailed reaction mechanism and the origins of site selectivity and diastereoselectivity.