Hydroxylamines As Bifunctional Single-Nitrogen Sources for the Rapid Assembly of Diverse Tricyclic Indole Scaffolds Liangxin Fan Jiamao Hao Jingxun Yu Xiaojun Ma Jingjing Liu Xinjun Luan 10.1021/jacs.0c00403.s008 https://acs.figshare.com/articles/dataset/Hydroxylamines_As_Bifunctional_Single-Nitrogen_Sources_for_the_Rapid_Assembly_of_Diverse_Tricyclic_Indole_Scaffolds/12037485 Conventional approaches on using hydroxylamine derivatives as single nitrogen sources, for the construction of <i>n</i>-membered (<i>n</i> > 3) N-heterocycles, rely upon two chemical operations by involving sequential nucleophilic and electrophilic C–N bond formations. Here, we report a highly efficient cascade of alkyne insertion/C–H activation/amination for the rapid preparation of a myriad of tricyclic indoles, in a single-step transformation, by using bifunctional secondary hydroxylamines. It is noteworthy that judicious selection of applicable amino agents, for enabling the prior oxidative addition of aryl iodide to initial Pd(0) species and subsequent two C–N bonds formation, was the key to the success of this reaction. Control experiments indicated that a five-membered palladacyclic intermediate played a crucial role in promoting the final aminative ring closure. 2020-03-26 20:44:46 insertion sequential nucleophilic Rapid Assembly alkyne Diverse Tricyclic Indole Scaffolds Bifunctional Single-Nitrogen Sources N-heterocycle hydroxylamine derivatives aryl iodide electrophilic species control experiments role aminative ring closure five-membered palladacyclic approach transformation chemical operations activation construction formation tricyclic indoles bifunctional nitrogen sources Hydroxylamine preparation cascade oxidative addition agent Pd bond