A Tandem Madelung Indole Synthesis Mediated by a LiN(SiMe<sub>3</sub>)<sub>2</sub>/CsF System
Ruyuan Ma, Yan‐En Wang, Dan Xiong, Jianyou Mao
Abstract
A tandem Madelung indole synthesis by the reaction of methyl benzoate and N -methyl- o -toluidine has been discovered. The combination of LiN(SiMe 3 ) 2 with CsF is the key factor, which secures the high efficiency of such tandem transformations. Simply combining methyl benzoate, N -methyl- o -toluidine LiN(SiMe 3 ) 2, and CsF generated a diverse array of N -methyl-2-phenylindoles (31 examples, 50–90% yields). Furthermore, the scalability and the poststructural modifications of this indole synthesis were demonstrated.
Topics & Concepts
ChemistryTandemIndole testStereochemistryCombinatorial chemistryMaterials scienceComposite materialCatalytic Cross-Coupling ReactionsCatalytic C–H Functionalization MethodsCoordination Chemistry and Organometallics