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Amine-Directed Diverse C(sp3)-H Functionalization (Amine-FUNC)
Start date: Apr 1, 2015, End date: Mar 31, 2017 PROJECT  FINISHED 

The development of new chemical transformations based on catalytic functionalization of unactivated C-H bonds has the potential to simplify the synthesis of complex molecules dramatically. Although some progress have been achieved in this emerging area, the selective transformation of aliphatic C-H bonds is still a challenge. This proposal aims to develop a new platform for the direct activation of unactivated sp3 C-H bonds of aliphatic amines and to apply this novel C(sp3)-H functionalization technology to synthesize diverse amine compounds. A key novel concept of this project is to use an unprotected aliphatic secondary amine as a native directing group, through a remarkable 4-membered-ring cyclometallation pathway. The goals of this proposal include: (I) developing unprecedented diverse C(sp3)-H functionalization of amine technology, accessing diverse functionalized amine compounds, (II) developing novel Pd-catalyzed enantioselective C-H functionalization methods to make enantioenriched chiral molecules, (III) application of this novel C(sp3)-H functionalization technology to make a library of diverse functionalized Salbutamol and Bupropion analogues, and screen them for biological and medicinal activities.
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