Deoxygenative alkylation of tertiary amides using alkyl iodides under visible light

It is an unceasing goal for organic chemists to develop new catalytic methodologies for functional group transformations of widespread molecular structures. Amides are readily available from simple and reliable reactions, which are common structural units found in biologically active compounds. Consequently, they are attractive to be exploited in amine synthesis by reductive cross coupling. However, deoxygenative functionalization of amides is a long-standing challenge owing to the inertness of the resonance-stabilized amide C=O bond. In this work, a deoxygenative alkylation strategy was demonstrated, which combines amides and alkyl iodides to build structurally diverse tertiary alkylamines in a single step. Compared with previous deoxygenative alkylation of amides using organometallic reagents as functional partner, this work uses stable and easily available alkyl halides as functionalization reagents. The versatile and flexible strategy plus structural and functional diversity of readily available amides and alkyl iodides renders it highly appealing for the streamlined synthesis of tertiary amines and would be of much interest in areas such as pharmaceutical and agrochemical research.