Enforced Electronic-Donor-Acceptor Complex Formation in Water for Photochemical Cross-Coupling

The amino alcohol meglumine solubilizes organic compounds in water and enforces the formation of electron donor acceptor (EDA) complexes of haloarenes with indoles, anilines, anisoles or thiols, which are not observed in organic solvents. UV-A photoinduced electron transfer within the EDA complexes induces the mesolytic cleavage of the halide ion and radical recombination of the arenes leading, after rearomatization and proton loss to C -C or C -S coupling products. Depending on the substitution pattern selective and unique cross-couplings are observed. UV and NMR measurements reveal the importance of the assembly for the photoinduced reaction. Enforced EDA aggregate formation in water allows new activation modes for organic photochemical synthesis.

Automated summary

The amino alcohol meglumine solubilizes organic compounds in water and enforces the formation of electron donor acceptor (EDA) complexes, resulting in unique cross-coupling reactions. UV-A photoinduced electron transfer within the EDA complexes leads to the cleavage of halide ions and recombination of arenes, followed by rearomatization and proton loss. UV and NMR measurements demonstrate the significance of the EDA aggregates for the photoinduced reaction. Enforced EDA aggregate formation in water provides new activation modes for organic photochemical synthesis.