Iron-Catalyzed C(sp3)−H Functionalization of N,N-Dimethylanilines with Isocyanides

Abstract

An efficient ligand-free Fe-catalyzed oxidative Ugi-type reaction toward the assembly of α-amino amides and short peptides is described. The reaction proceeds through the α-C(sp3)−H oxidation of N,N-dimethylanilines and further nucleophilic attack of the resulting iminium species by isocyanides. Additive screening showed that judicious choice of the carboxylic acid could lead to the formation of α-amino imides via a 3-component reaction. The process occurs with operational simplicity and is compatible with a variety of sensitive functional groups.We thank for technical and human support provided by Central Service of Analysis de Alava–SGIker of UPV/EHU. We are grateful to Gobierno Vasco (IT_1033-16) and MINECO (CTQ2016-78395-P) for financial support. A. C. thanksMINECO for a Ramón y Cajal research contract (RYC-2012-09873). Cost-CHAOS action (CA15106) is also acknowledge