A General Approach to Creating Soluble Catalytic Polymers Heterogenized in Microcapsules

A general method for preparing site-isolated polymeric catalysts is presented. Linear chloromethyl and azide polymers have been sequestered within polyurea microcapsules and small molecule catalysts soaked through the shell walls to functionalize the soluble polymers. Reaction onto each type of supp...

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Published inOrganic letters Vol. 9; no. 17; pp. 3449 - 3451
Main Authors Mason, Brian P, Bogdan, Andrew R, Goswami, Anandarup, McQuade, D. Tyler
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 16.08.2007
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Abstract A general method for preparing site-isolated polymeric catalysts is presented. Linear chloromethyl and azide polymers have been sequestered within polyurea microcapsules and small molecule catalysts soaked through the shell walls to functionalize the soluble polymers. Reaction onto each type of support is quantitative and MacMillan, DMAP, and TEMPO test catalysts are shown to have faster reaction rates than the analogous resin-supported catalysts.
AbstractList A general method for preparing site-isolated polymeric catalysts is presented. Linear chloromethyl and azide polymers have been sequestered within polyurea microcapsules and small molecule catalysts soaked through the shell walls to functionalize the soluble polymers. Reaction onto each type of support is quantitative and MacMillan, DMAP, and TEMPO test catalysts are shown to have faster reaction rates than the analogous resin-supported catalysts.
Author Goswami, Anandarup
McQuade, D. Tyler
Bogdan, Andrew R
Mason, Brian P
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Cites_doi 10.1021/ja00897a025
10.1021/ja000092s
10.1002/adsc.200606043
10.1002/anie.200603854
10.1021/cr010440o
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References Scher H. B. (ol071360vb00007/ol071360vb00007_1) 1981
Gheorghe A. (ol071360vb00014/ol071360vb00014_1) 2006; 348
Puglisi A. (ol071360vb00009/ol071360vb00009_1) 2004; 567
Merrifield R. B. (ol071360vb00003/ol071360vb00003_1) 1963; 85
Malagu K. (ol071360vb00006/ol071360vb00006_1) 2002; 316
Price K. E. (ol071360vb00002/ol071360vb00002_1) 2006; 39
Demko Z. P. (ol071360vb00010/ol071360vb00010_1) 2002; 41
Wang Q. (ol071360vb00011/ol071360vb00011_1) 2005; 2
Sterling J. (ol071360vb00013/ol071360vb00013_1) 2006; 025446
Price K. E. (ol071360vb00001/ol071360vb00001_1) 2006; 128
Bogdan A. R. (ol071360vb00012/ol071360vb00012_1) 2007; 46
Benaglia M. (ol071360vb00004/ol071360vb00004_1) 2003; 103
Chen S. Q. (ol071360vb00005/ol071360vb00005_1) 1997; 119
Ahrendt K. A. (ol071360vb00008/ol071360vb00008_1) 2000; 122
References_xml – volume: 128
  start-page: 10377
  year: 2006
  ident: ol071360vb00001/ol071360vb00001_1
  publication-title: J. Am. Chem. Soc.
  contributor:
    fullname: Price K. E.
– volume: 567
  start-page: 573
  year: 2004
  ident: ol071360vb00009/ol071360vb00009_1
  publication-title: Eur. J. Org. Chem.
  contributor:
    fullname: Puglisi A.
– volume: 119
  start-page: 8725
  year: 1997
  ident: ol071360vb00005/ol071360vb00005_1
  publication-title: J. Am. Chem. Soc.
  contributor:
    fullname: Chen S. Q.
– volume: 85
  start-page: 2154
  year: 1963
  ident: ol071360vb00003/ol071360vb00003_1
  publication-title: J. Am. Chem. Soc.
  doi: 10.1021/ja00897a025
  contributor:
    fullname: Merrifield R. B.
– volume: 122
  start-page: 4244
  year: 2000
  ident: ol071360vb00008/ol071360vb00008_1
  publication-title: J. Am. Chem. Soc.
  doi: 10.1021/ja000092s
  contributor:
    fullname: Ahrendt K. A.
– volume: 025446
  start-page: 2006
  year: 2006
  ident: ol071360vb00013/ol071360vb00013_1
  publication-title: Patent Appl.
  contributor:
    fullname: Sterling J.
– volume: 316
  start-page: 318
  year: 2002
  ident: ol071360vb00006/ol071360vb00006_1
  publication-title: Synlett
  contributor:
    fullname: Malagu K.
– volume: 2
  start-page: 301
  year: 2005
  ident: ol071360vb00011/ol071360vb00011_1
  publication-title: Lett. Org. Chem.
  contributor:
    fullname: Wang Q.
– volume: 348
  start-page: 1020
  year: 2006
  ident: ol071360vb00014/ol071360vb00014_1
  publication-title: Adv. Synth. Catal.
  doi: 10.1002/adsc.200606043
  contributor:
    fullname: Gheorghe A.
– volume-title: Aug 25
  year: 1981
  ident: ol071360vb00007/ol071360vb00007_1
  contributor:
    fullname: Scher H. B.
– volume: 46
  start-page: 1701
  year: 2007
  ident: ol071360vb00012/ol071360vb00012_1
  publication-title: Angew. Chem., Int. Ed.
  doi: 10.1002/anie.200603854
  contributor:
    fullname: Bogdan A. R.
– volume: 103
  start-page: 3429
  year: 2003
  ident: ol071360vb00004/ol071360vb00004_1
  publication-title: Chem. Rev.
  doi: 10.1021/cr010440o
  contributor:
    fullname: Benaglia M.
– volume: 39
  start-page: 7685
  year: 2006
  ident: ol071360vb00002/ol071360vb00002_1
  publication-title: Macromolecules
  contributor:
    fullname: Price K. E.
– volume: 41
  start-page: 2116
  year: 2002
  ident: ol071360vb00010/ol071360vb00010_1
  publication-title: Angew. Chem., Int. Ed.
  contributor:
    fullname: Demko Z. P.
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Snippet A general method for preparing site-isolated polymeric catalysts is presented. Linear chloromethyl and azide polymers have been sequestered within polyurea...
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Title A General Approach to Creating Soluble Catalytic Polymers Heterogenized in Microcapsules
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