Photocatalytic Terminal C−C Coupling Reaction Inside Water Soluble Nanocages

Abstract

Developing methods that activate C-H bonds directly with high selectivity for C-C bond formation in complex organic synthesis has been a major chemistry challenge. Recently it has been shown that photoactivation of weakly polarized C-H bonds can be carried out inside a cationic water-soluble nanocage with visible light-mediated host-guest charge transfer (CT) chemistry. Using this novel photoredox activation paradigm, here we demonstrate C-C bond formation to photo-generate 1,3-diynes at room temperature in water from terminal aromatic alkynes for the first time. The formation of cavity-confined alkyne radical cation and the proton-removed neutral radical species highlight the unique C-C coupling step driven by supramolecular preorganization.