The Aza‐Morita–Baylis–Hillman Reaction: A Mechanistic and Kinetic Study |
| |
| Authors: | Dr Christoph Lindner Dr Yinghao Liu Prof Konstantin Karaghiosoff Dr Boris Maryasin Prof Hendrik Zipse |
| |
| Institution: | Department of Chemistry, LMU Munich, Butenandtstrasse 5‐13, 81377 München (Germany), Fax: (+49)?89‐2180‐77738 |
| |
| Abstract: | The aza‐Morita‐Baylis–Hillman (aza‐MBH) reaction has been studied in a variety of solvents, a selection of imine substrates and with various combinations of PPh3 and para‐nitrophenol as the catalyst system. The measured kinetic data indicates that the effects of solvent and protic co‐catalyst are strongly interdependent. These results are most easily reconciled with a mechanistic model involving the reversible protonation of zwitterionic intermediates in the catalytic cycle, which is also supported by 31P NMR spectroscopy and quantum chemical studies. |
| |
| Keywords: | kinetics Lewis bases NMR spectroscopy reaction mechanisms solvent effects synthetic methods |
|
