Copper/Titanium Catalysis Forms Fully Substituted Carbon Centers from the Direct Coupling of Acyclic Ketones, Amines, and Alkynes


  • Acknowledgement is made to the Donors of the American Chemical Society Petroleum Research Fund for partial support of this research. Additional support was provided by the University of California, Riverside, and M.N. was awarded a Dean’s Summer Undergraduate Research Fellowship. We thank Mr. Daniel Reza for assistance.


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Three-component coupling, with a pair: The combination of CuII and TiIV catalyzes the first three-component coupling of unactivated ketones with a diverse range of amines and terminal alkynes. Tetrasubstituted propargylamines are formed under green, solvent-free conditions (see scheme). This dual metal system overcomes the barrier to ketimine formation and subsequent attack, opening a new path to multicomponent reactions of ketone electrophiles.