Tetraarylphosphonium Salts as Solubility-Control Groups: Phosphonium-Supported Triphenylphosphine and Azodicarboxylate Reagents

Predictable solubilities! Reagents supported on a tetraarylphosphonium group have solubilities that can be predicted. The reagents and their by‐products can be readily removed, recovered, and recycled after reaction by a precipitation/filtration sequence initiated by the addition of a low‐polarity s...

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Published inAngewandte Chemie International Edition Vol. 45; no. 9; pp. 1415 - 1420
Main Authors Poupon, Jean-Christophe, Boezio, Alessandro A., Charette, André B.
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 20.02.2006
WILEY‐VCH Verlag
Wiley
Subjects
Chemistry
Chemistry, Multidisciplinary
phosphonium ions
phosphorus
Physical Sciences
Science & Technology
separation
supported catalysts
Wittig reaction
Wittig reaction
ORGANIC-SYNTHESIS
SOLUBLE POLYMERS
RAPID PURIFICATION
OLEFIN METATHESIS
supported catalysts
RUTHENIUM CARBENE COMPLEX
FUNCTIONALIZED POLYMERS
MITSUNOBU REACTION
separation
COMBINATORIAL SYNTHESIS
RECOVERABLE CATALYSTS
phosphonium ions
phosphorus
CHIRAL CATALYSTS
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ISSN1433-7851
1521-3773
DOI10.1002/anie.200503599

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Summary:Predictable solubilities! Reagents supported on a tetraarylphosphonium group have solubilities that can be predicted. The reagents and their by‐products can be readily removed, recovered, and recycled after reaction by a precipitation/filtration sequence initiated by the addition of a low‐polarity solvent, such as diethyl ether. Furthermore, the supported reagents are robust and exhibit reactivities similar to their parent compounds.
Bibliography:This work was supported by Valorisation-Recherche Québec (VRQ), Valorisation-Recherche s.e.c. (Univalor), and the Université de Montréal. A.A.B. is grateful to the NSERC (PGF B) and FCAR (B2) for postgraduate fellowships.
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ArticleID:ANIE200503599
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This work was supported by Valorisation‐Recherche Québec (VRQ), Valorisation‐Recherche s.e.c. (Univalor), and the Université de Montréal. A.A.B. is grateful to the NSERC (PGF B) and FCAR (B2) for postgraduate fellowships.
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ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200503599