Copper Catalyzed C-H Functionalization: Method Development via Enabling Intermediates

Catalytic C-H functionalization offers the promise of atom economical introduction of functionality into organic molecules by direct transformation of C-H bonds to C-C, C-N, or C-O bonds.  Compared to more traditional approaches that involve functional group manipulations, the direct utilization of C-H bonds in synthesis can minimize chemical steps, economic cost, and environmental impact.

 

Employing an inexpensive copper-based catalyst system, we have employed both organoazides as well as alkyl- and arylamines in sp3 C-H amination. Experimental and theoretical insights into the mechanism of C-H amination by our -diketiminato copper(I) catalyst system have revealed three different classes of H-atom abstracting species.  Combining these mechanistic findings with efficient radical capture by copper(II) intermediates has resulted in a range of new catalytic C-H functionalization reactions that result in C-N, C-O, C-S and C-C bond formation, including the use of alcohols and phenols in sp3 C-H etherification.

Division(s): Inorganic

Speaker: Tim Warren

Speaker Institution: Georgetown University

Event Date: 03-28-2017

Event Time: 4:00 PM

Event Location: Chemistry A101

Mixer Time: 3:45 PM

Mixer Location: Chemistry B101E

Host: E. Chen