Tue, Mar. 3, 2015, 4:30pm - 6:00pm
Frick Chemistry Laboratory, Taylor Auditorium
Host: David MacMillan
Direct Catalytic Synthesis of Tetrasubstituted Carbons Bearing Amines and Heteroaromatics
The direct formation of tetrasubstituted carbons bearing amines is rare—especially compared to the wide array of trisubstituted products accessible from multicomponent couplings of aldehydes, amines, and nucleophiles. Dual copper/titanium catalysis is required to overcome the barrier to condensation of a ketone with an amine and subsequent alkynylation, and copper-catalyzed Markovnikov alkyne hydroamination provides a unique alternate pathway to tetrasubstituted propargylamines. In addition, green solvent-free conditions provide one-step syntheses of alkyl- and pyridyl-substituted quinolines.