Catalytic C-H functionalization offers the promise of atom economical introduction of molecular diversity 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 β-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, and C-C bond formation, including the use of alcohols and phenols in sp3 C-H etherification.

Copper catalyzed C-H functionalization: Method development via enabling intermediates

254th National Meeting (2017)

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