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Thermomorphic fluorous phosphines as organocatalysts for Michael addition reactions |
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| Authors: | Carolina Gimbert John A Gladysz Markus Jurisch |
| Institution: | a Department of Chemistry, Universitat Autònoma de Barcelona, 08193 Cerdanyola del Vallès, Spain b Department of Chemistry, Texas A&M University, PO Box 30012, College Station, TX 77842-3012, USA c Institut für Organische Chemie and Interdisciplinary Center for Molecular Materials, Friedrich-Alexander-Universität Erlangen-Nürnberg, Henkestraße 42, 91054 Erlangen, Germany |
| Abstract: | The fluorous phosphines P(CH2)mRfn]3 (Rfn = (CF2)n−1CF3; m/n = 2/8, 3/8, 3/10) are efficient nucleophilic catalysts of Michael addition reactions. They can be easily recycled based upon their highly temperature-dependent solubilities (thermomorphism), with recovery by simple liquid/solid phase separation. The phosphonium salt formed by reaction of the nucleophilic phosphine with the α,β-unsaturated system appears to be a significant component of the catalyst rest state. |
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