The ability to perform C-C cross-coupling reaction has largely been enabled by systems incorporating organometallic reagents and activated C-H sp3 compounds. The ability to perform similar coupling reactions with un-activated C-H sp3 carbons, however, still remains to be a grand challenge. We have successfully demonstrated the amination and etherification of un-activated C-H sp3 bonds via the copper (I) β-diketiminato catalytic system. Our recent development of systems incorporating a copper (I) β-diketiminato catalyst in the presence of di-tert-butylperoxide oxidant show successful formation of C(sp3)-C(sp) bonds via the coupling of an alkyne and an un-activated C-H sp3 bonds in moderate to high yields. More importantly, our catalytic system is effective in the formation of C(sp3)-C(sp3) bonds via the coupling of C-H sp3 compounds and acidic sp3 C-H molecules. As a result, new frontiers for the formation of C-C sp3 bonds can be explored.

Copper catalyzed functionalization of un-activated sp3 C-H bonds via carbon-carbon bond formation

254th National Meeting (2017)

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