A Halogen-Atom Transfer (XAT)-Based Approach to Indole Synthesis Using Aryl Diazonium Salts and Alkyl Iodides
Sebastian Govaerts, Kento Nakamura, Timothée Constantin, Daniele Leonori
Abstract
-heterocycles in pharmaceuticals. Here, we present an alternative to the classic Fischer indole synthesis based on the radical coupling between aryl diazoniums and alkyl iodides. This iron-mediated strategy features a double role for the aryl diazoniums that sequentially activate the alkyl iodides through halogen-atom transfer and then serve as radical acceptors. The process operates under mild conditions and enables the preparation of densely functionalized indoles.
Topics & Concepts
ChemistryAlkylArylHalogenIndole testCombinatorial chemistryAryl radicalOrganic chemistryRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques