Abstract
The effects of electronic and steric properties of phosphorus ligands on Heck reactions in supercritical CO2 and non-polar hydrocarbon solvents were studied. In Heck reactions between iodobenzene and butyl acrylate, higher yields were obtained with less electron-rich phosphine ligands. This trend was also observed with the electron-poor triphenyl phosphite. A range of sterically demanding phosphites were then investigated. Biphenyl-containing phosphites 8 and 13 were found to be highly effective. In the Heck reaction between the less-reactive bromobenzene and butyl acrylate, the bulky, electron-rich tri-tert-butylphosphine ligand produced the best yield. These results emphasize the importance of both electronic and steric properties of phosphorus ligands in the Heck reaction in non-polar solvents.
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