Functionalization of carbon-hydrogen bonds of hydrocarbons and ethers via carbene insertion with copper(I)-homoscorpionate catalysts

Complexes of general formula Tp(x)Cu (Tp(x) = homoscorpionate ligand) have been employed as catalysts for the insertion of ethyl diazoacetate into C-H bonds of a variety of hydrocarbons and ethers, in moderate to high yields: tertiary, secondary, and primary C-H bonds have been functionalized by this methodology. Particularly interesting is the homologation of O-methyl groups in ethers, which has been achieved for a group of substrates. The existence of electron-withdrawing groups in the Tpx ligand seems to be crucial for the activity and the selectivity of the catalyst.