Functionalization of Carbon−Hydrogen Bonds of Hydrocarbons and Ethers via Carbene Insertion with Copper(I)−Homoscorpionate Catalysts

Abstract

Complexes of general formula TpxCu (Tpx = 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.