A Halogen-Atom Transfer (XAT)-Based Approach to Indole Synthesis Using Aryl Diazonium Salts and Alkyl Iodides

Organic Letters, vol. 24, pp. 7883–7887

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.

Authors 4

1. Sebastian Govaerts

   University of Manchester

   Affiliation as printed

   Department of Chemistry, University of Manchester, Oxford Road, Manchester M13 9PL, U.K

2. Kento Nakamura

   University of Manchester

   Affiliation as printed

   Department of Chemistry, University of Manchester, Oxford Road, Manchester M13 9PL, U.K

3. Timothée Constantin corresponding

   University of Manchester

   Affiliation as printed

   Department of Chemistry, University of Manchester, Oxford Road, Manchester M13 9PL, U.K

4. Daniele Leonori corresponding Aachen Institute of Organic Chemistry

   RWTH Aachen University

   Affiliation as printed

   Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, Aachen 52056, Germany