|
A Study of the Heck Reaction in Non-Polar Hydrocarbon Solvents and in Supercritical Carbon Dioxide
Jin-Kyun
Lee A B,
Rachel M.
Williamson C,
Andrew B.
Holmes A C E,
Edward J.
Bush D,
Ian F.
McConvey D
A
Melville Laboratory for Polymer Synthesis, Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, UK.
B
Department of Materials Science and Engineering, Cornell University, Ithaca, NY 14853, USA.
C
School of Chemistry, Bio21 Institute, University of Melbourne, VIC 3010, Australia.
D
Process R&D, AstraZeneca Pharmaceuticals, Silk Road Business Park, Macclesfield, Cheshire SK10 2NA, UK.
E
Corresponding author. Email: aholmes@unimelb.edu.au
|  |
|
Australian Journal of Chemistry 60(8) 566–571 http://dx.doi.org/10.1071/CH07160
Submitted: 18 May 2007
Accepted: 28 June 2007
Published online: 9 August 2007
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.
|
|
|
 |
Subscriber Login |
 |
|
Early Alert
Connect with us
