Liangxin Fan, J. Hao, Jingxun Yu
Mar 17, 2020
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0
Influential Citations
41
Citations
Journal
Journal of the American Chemical Society
Abstract
Conventional approaches on using hydroxylamine derivatives as single nitrogen sources, for the construction of n-membered (n>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. Noteworthy, 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 five-membered palladacyclic intermediate played a crucial role in promoting the final aminative ring closure.