SYNTHESIS OF DIARYL ETHERS USING AN EASY-TO-PREPARE, AIR-STABLE, SOLUBLE COPPER(I) CATALYST

Abstract

We have found that bromo(triphenylphosphine)copper(I), an air-stable and soluble copper(I) complex, can be used as a catalyst in the synthesis of diaryl ethers. Using this catalyst, we have synthesized diaryl ethers from electron-rich aryl bromides and electron-rich phenols in the presence of cesium carbonate, in 17–24 h, in NMP. We also found that electron-deficient aryl bromides couple with phenols in the presence of cesium carbonate, in 6 h in NMP at 70°C, without the catalyst.

ACKNOWLEDGMENTS

The University of Massachusetts, Amherst start-up funds provided the financial support for this research. DV gratefully acknowledges a Camille and Henry Dreyfus New Faculty Award. We thank Dr. Greg Dabkowski of the Microanalysis lab at the UMass-Amherst for elemental analyses and the University of Massachusetts Chemistry Department X-ray Structural Laboratory supported by National Science Foundation grant CHE-9974648 for assistance with the crystallographic analyses.