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The aza-Morita-Baylis-Hillman reaction: a mechanistic and kinetic study
Christoph Lindner1, Yinghao Liu, Konstantin Karaghiosoff
1Department of Chemistry, LMU Munich, Butenandtstrasse 5-13, 81377 München, Germany.
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 (31)P NMR spectroscopy and quantum chemical studies.
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