Amines and imines are two of most common motifs in active pharmaceuticals, but their traditional syntheses often require toxic alkyl halides and aldehydes. While alcohol-amine coupling reactions are now more common, reactions of exclusively amine partners reacting without oxidants are not known.  In an effort to develop atom-economical methods for synthesis of imines and amines from more benign starting materials, we have developed a method for acceptorless dehydrogenative coupling of amines to selectively form imines and amines using low-cost heterogeneous catalysts. The catalysts consist of palladium and iron-doped layered double hydroxides, and have been characterized by an array of methods in an effort to elucidate structure-activity relationships and the catalytically active species. The selectivity of the reaction can be controlled by small changes to the catalyst and reaction conditions. The substrate scope and selectivity obtained for different substrates are explored, as are experiments to probe mechanism of this reaction. The recyclability of the catalysts is also discussed.

Catalytic dehydrogenative coupling of amines

254th National Meeting (2017)

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