Copper(II)-catalyzed C-H (sp3) oxidation and C-N cleavage: Synthesis of methylene-bridged compounds using TMEDA as a carbon source in water

Article abstract of DOI:10.1039/c3ra40695d

A green, simple, and efficient protocol for the selective methylenation via CuCl₂/oxygen-mediated C-H (sp³) oxidation and C-N cleavage using tetramethylethylenediamine (TMEDA) as a carbon source has been developed. The reactions were achieved in green solvent water under atmospheric conditions. The protocol exhibited a broad substrate scope including indoles, anilines, pyrroles and 1,3-dicarbonyls. Furthermore, two key intermediates of the reaction were successfully identified and the mechanism was explored. The Royal Society of Chemistry 2013.