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Iron-catalyzed C(sp3)-H functionalization of N,N-dimethylanilines with isocyanides
Itziar Guerrero1, Marcos San Segundo1, Arkaitz Correa1
1Department of Organic Chemistry I, University of the Basque Country (UPV/EHU), Joxe Mari Korta R&D Center, Avda. Tolosa 72, 20018 Donostia-San Sebastián, Spain. arkaitz.correa@ehu.es.
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.
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