Thermomorphic fluorous phosphines as organocatalysts for Michael addition reactions

Carolina Gimbert; Adelina Vallribera; John A. Gladysz; Markus Jurisch

doi:10.1016/j.tetlet.2010.06.136

Thermomorphic fluorous phosphines as organocatalysts for Michael addition reactions

Carolina Gimbert, Adelina Vallribera, John A. Gladysz, Markus Jurisch

Department of Chemistry

Research output: Contribution to journal › Article › Research › peer-review

10 Citations (Scopus)

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. © 2010 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	4662-4665
Journal	Tetrahedron Letters
Volume	51
Issue number	35
DOIs	https://doi.org/10.1016/j.tetlet.2010.06.136
Publication status	Published - 1 Sept 2010

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10.1016/j.tetlet.2010.06.136

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title = "Thermomorphic fluorous phosphines as organocatalysts for Michael addition reactions",

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. {\textcopyright} 2010 Elsevier Ltd. All rights reserved.",

author = "Carolina Gimbert and Adelina Vallribera and Gladysz, {John A.} and Markus Jurisch",

year = "2010",

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doi = "10.1016/j.tetlet.2010.06.136",

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T1 - Thermomorphic fluorous phosphines as organocatalysts for Michael addition reactions

AU - Gimbert, Carolina

AU - Vallribera, Adelina

AU - Gladysz, John A.

AU - Jurisch, Markus

PY - 2010/9/1

Y1 - 2010/9/1

N2 - 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. © 2010 Elsevier Ltd. All rights reserved.

AB - 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. © 2010 Elsevier Ltd. All rights reserved.

U2 - 10.1016/j.tetlet.2010.06.136

DO - 10.1016/j.tetlet.2010.06.136

M3 - Article

SN - 0040-4039

VL - 51

SP - 4662

EP - 4665

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 35

ER -

Thermomorphic fluorous phosphines as organocatalysts for Michael addition reactions

Abstract

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