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
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Online AccessGet full text
ISSN1433-7851
1521-3773
DOI10.1002/anie.200503599

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Abstract 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.
AbstractList 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.
Author Charette, André B.
Boezio, Alessandro A.
Poupon, Jean-Christophe
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  givenname: Jean-Christophe
  surname: Poupon
  fullname: Poupon, Jean-Christophe
  organization: Département de Chimie, Université de Montréal, P.O. Box 6128, Station Downtown, Montréal, Québec H3C 3J7, Canada, Fax: (+1) 514-343-5900
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  givenname: Alessandro A.
  surname: Boezio
  fullname: Boezio, Alessandro A.
  organization: Département de Chimie, Université de Montréal, P.O. Box 6128, Station Downtown, Montréal, Québec H3C 3J7, Canada, Fax: (+1) 514-343-5900
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  givenname: André B.
  surname: Charette
  fullname: Charette, André B.
  email: andre.charette@umontreal.ca
  organization: Département de Chimie, Université de Montréal, P.O. Box 6128, Station Downtown, Montréal, Québec H3C 3J7, Canada, Fax: (+1) 514-343-5900
BackLink https://www.ncbi.nlm.nih.gov/pubmed/16425329$$D View this record in MEDLINE/PubMed
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Issue 9
Keywords 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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Notes 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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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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2002 2002; 114 41
1965; 14
2004; 29
1963; 85
1995; 36
2004; 69
1996 2000 2000; 118 112 39
2004; 6
2000; 2
1999; 40
1960; 82
1981; 81
2000
1997; 97
1999; 19
2001 2001; 113 40
2002; 102
2003; 6
1978; 63
2003; 9
1999; 99
1999; 55
2003; 5
2000; 122
2005; 38
2003; 125
1972; 13
1962; 84
1989
2004 2004; 116 43
2001; 123
2004; 104
1966 1948; 99 70
2002; 9
1991; 32
1999; 28
1998
1997
1996; 52
1999; 64
2004
2003
1999; 1
2001; 66
1999
2004; 10
1990; 20
2003 2003; 115 42
2000; 33
2005; 127
1969; 69
1999; 32
1994; 59
2000; 100
1998 1998; 110 37
2003; 103
2000 2000; 112 39
1998; 9
e_1_2_2_24_2
e_1_2_2_47_2
Bhalay G. (e_1_2_2_21_2) 2000
e_1_2_2_6_2
e_1_2_2_20_2
e_1_2_2_2_2
e_1_2_2_62_2
e_1_2_2_85_2
e_1_2_2_28_2
e_1_2_2_43_2
e_1_2_2_66_2
e_1_2_2_89_2
e_1_2_2_81_2
e_1_2_2_13_2
e_1_2_2_36_2
e_1_2_2_59_2
e_1_2_2_51_2
e_1_2_2_74_2
e_1_2_2_74_3
e_1_2_2_51_3
e_1_2_2_17_2
e_1_2_2_32_2
e_1_2_2_55_2
e_1_2_2_78_2
e_1_2_2_55_3
e_1_2_2_70_2
e_1_2_2_48_2
e_1_2_2_5_2
e_1_2_2_1_2
e_1_2_2_29_4
e_1_2_2_40_2
e_1_2_2_86_2
e_1_2_2_29_3
e_1_2_2_29_2
e_1_2_2_63_2
e_1_2_2_44_2
e_1_2_2_9_3
e_1_2_2_9_2
e_1_2_2_25_2
e_1_2_2_82_2
e_1_2_2_37_2
e_1_2_2_10_3
e_1_2_2_79_3
e_1_2_2_10_2
e_1_2_2_75_2
e_1_2_2_18_2
e_1_2_2_52_2
e_1_2_2_33_2
e_1_2_2_79_2
e_1_2_2_14_2
e_1_2_2_56_2
e_1_2_2_71_2
e_1_2_2_90_2
e_1_2_2_4_2
e_1_2_2_22_2
e_1_2_2_49_2
e_1_2_2_49_3
e_1_2_2_41_2
e_1_2_2_64_2
e_1_2_2_83_2
e_1_2_2_8_2
e_1_2_2_26_2
e_1_2_2_45_2
e_1_2_2_68_2
e_1_2_2_87_2
e_1_2_2_60_2
e_1_2_2_11_2
Harned A. M. (e_1_2_2_38_2) 2005; 38
e_1_2_2_72_2
e_1_2_2_19_2
e_1_2_2_30_2
e_1_2_2_53_2
e_1_2_2_53_3
e_1_2_2_15_2
e_1_2_2_34_2
e_1_2_2_57_2
e_1_2_2_76_2
e_1_2_2_91_2
e_1_2_2_3_2
Maercker A. (e_1_2_2_67_2) 1965; 14
e_1_2_2_23_2
e_1_2_2_69_2
e_1_2_2_61_2
e_1_2_2_42_2
e_1_2_2_84_2
e_1_2_2_7_2
e_1_2_2_27_2
e_1_2_2_65_2
e_1_2_2_46_2
e_1_2_2_88_2
e_1_2_2_80_2
e_1_2_2_12_2
e_1_2_2_58_2
e_1_2_2_39_2
e_1_2_2_50_2
e_1_2_2_31_2
e_1_2_2_73_2
e_1_2_2_16_2
e_1_2_2_54_2
e_1_2_2_35_2
e_1_2_2_77_2
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Snippet Predictable solubilities! Reagents supported on a tetraarylphosphonium group have solubilities that can be predicted. The reagents and their by‐products can be...
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SubjectTerms Chemistry
Chemistry, Multidisciplinary
phosphonium ions
phosphorus
Physical Sciences
Science & Technology
separation
supported catalysts
Wittig reaction
Title Tetraarylphosphonium Salts as Solubility-Control Groups: Phosphonium-Supported Triphenylphosphine and Azodicarboxylate Reagents
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