Student or educator? Sign up with your school email and get 6 months of Pro free.
CoChat
Sign Up
Cited by 301

The DOI matches its Crossref record; 1 of the 1 references it cites were found in a registry or an index.

In Situ Generation of Carbenes: A General and Versatile Platform for Organocatalytic Living Polymerization

Nyce, Gregory W., Glauser, Thierry, Connor, Eric F., Möck, Andreas, Waymouth, Robert M., Hedrick, James L.·2003·Journal of the American Chemical Society
DOI 10.1021/ja021084+
Open this paper in CoChat — free account

Abstract

A metal-free, organocatalytic approach to living polymerization using N-heterocyclic carbenes as nucleophilic catalysts generated and used in situ in a single-pot process is detailed. The N-heterocyclic carbene catalyst platform is extremely versatile, as the nature of the substituents has a pronounced effect of catalyst stability and activity toward different substrates. The generation of imidazolium- and thiazaolium-based carbenes was accomplished from the reaction of the corresponding salts with the appropriate bases. This allowed the rapid screening of libraries of catalysts that provided a basic understanding of catalyst structure (sterics, electronics, etc.) with the polymerization rate, control, substrate, and range of molecular weights. The imidazole-based catalysts were significantly more active toward ROP than the thiazolium-based analogues. No appreciable differences between imidazol-2-ylidene and imidazolin-2-ylidene catalysts were observed. Less sterically demanding carbenes were found to be more active toward ring-opening polymerization (ROP) than their sterically encumbered analogues for lactone polymerization. These data prompted the investigation of ionic liquid as a precatalyst reservoir in a phase-transfer polymerization with an immiscible THF solution of monomer and initiator. In situ activation of the ionic liquid generates carbene that migrates to the organic phase effecting living ROP. Precatalyst (ionic liquid) regeneration terminates polymerization. This simple reaction/recycle protocol readily allows repetitive ROPs from the ionic liquid using commercially available materials.

Overview

The claims and statistics of this paper haven’t been checked yet.

Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.

A few free checks a day · papers already verified open instantly · results are public

Integrity signals

Registry

Crossref · 10.1021/ja021084+

Cites

1 of 1 references verified0 citation errors · 0 not checkable

Statistics

Verification

Claims the paper makes

The claims and statistics of this paper haven’t been checked yet.

Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.

A few free checks a day · papers already verified open instantly · results are public

Self-check

Percentages, sums and reported differences re-computed from the paper’s own numbers.

The self-check needs the paper’s full text.

Citations

Cites

Show all 1 references

Research works printed but not linked: 84

  1. Borman S., 2002, Chem. Eng. News, 80, 33
  2. For, 2002, J. Am. Chem. Soc., 124, 7894, 10.1021/ja025981p · DOI
  3. Connor E. F., 2002, J. Am. Chem. Soc., 124, 914, 10.1021/ja0173324 · DOI
  4. Nyce G. W., 2002, Org. Lett., 4, 3587, 10.1021/ol0267228 · DOI · Paper page
  5. Grasa G. A., 2002, Org. Lett., 4, 3583, 10.1021/ol0264760 · DOI · Paper page
  6. Albertsson A.-C., 2002, Adv. Polym. Sci., 157
  7. Trollsås M., 1998, J. Am. Chem. Soc., 120, 4644, 10.1021/ja973678w · DOI · Paper page
  8. Trollsås M., 1998, Angew. Chem., Int. Ed., 37, 3132, 10.1002/(SICI)1521-3773(19981204)37:22<3132::AID-ANIE3132>3.0.CO;2-B · DOI
  9. For, 1995, J. Mater. Sci., Rev. Macromol. Chem. Phys., 35, 379, 10.1080/15321799508014594 · DOI
  10. Arduengo A. J., 1991, J. Am. Chem. Soc., 113, 361, 10.1021/ja00001a054 · DOI
  11. Arduengo A. J., 1992, J. Am. Chem. Soc., 114, 5530, 10.1021/ja00040a007 · DOI · Paper page
  12. Arduengo A., 1999, J. Acc. Chem. Res., 32, 913, 10.1021/ar980126p · DOI
  13. Arduengo A. J., 1998, Chem. Z., 32, 6
  14. Bourissou D., 2000, Chem. Rev., 100, 39, 10.1021/cr940472u · DOI
  15. Herrmann W., 1997, Angew. Chem., Int. Ed. Engl., 36, 2162, 10.1002/anie.199721621 · DOI
  16. Scholl M., 1999, Tetrahedron Lett., 40, 2247, 10.1016/S0040-4039(99)00217-8 · DOI
  17. Huang J., 1999, J. Am. Chem. Soc., 121, 2674, 10.1021/ja9831352 · DOI · Paper page
  18. Weskamp T., 1998, Angew. Chem., Int. Ed., 37, 2490, 10.1002/(SICI)1521-3773(19981002)37:18<2490::AID-ANIE2490>3.0.CO;2-X · DOI
  19. Herrmann W. A., 1995, J. Angew. Chem., Int. Ed. Engl., 34, 2371, 10.1002/anie.199523711 · DOI
  20. Herrmann W. A., 1996, Angew. Chem., Int. Ed. Engl., 35, 2805, 10.1002/anie.199628051 · DOI
  21. Lappert M., 1988, J. Organomet. Chem., 358, 185, 10.1016/0022-328X(88)87079-7 · DOI
  22. Enders D., 1995, Angew. Chem., Int. Ed. Engl., 34, 1021, 10.1002/anie.199510211 · DOI · Paper page
  23. For, 2001, J. Am. Chem. Soc., 123, 749, 10.1021/ja003582t · DOI
  24. For, 2000, Org. Lett., 2, 3153, 10.1021/ol0063510 · DOI
  25. Enders D., 1996, Helv. Chim. Acta, 79, 1217, 10.1002/hlca.19960790427 · DOI
  26. Enders D., 1996, Helv. Chim. Acta, 79, 1899, 10.1002/hlca.19960790712 · DOI
  27. Kerr M. S., 2002, J. Am. Chem. Soc., 124, 10298, 10.1021/ja027411v · DOI
  28. Enders D., 2002, Angew. Chem., Int. Ed., 41, 1743, 10.1002/1521-3773(20020517)41:10<1743::AID-ANIE1743>3.0.CO;2-Q · DOI
  29. Patten T., 1997, J. Am. Chem. Soc., 23, 65
  30. Coessens V., 2001, Prog. Polym. Sci., 26, 337, 10.1016/S0079-6700(01)00003-X · DOI
  31. Tokuchi K., 2000, Sci., Polym. Chem. Ed., 38, 4735, 10.1002/1099-0518(200012)38:1+<4735::AID-POLA130>3.0.CO;2-L · DOI
  32. Matyjaszewski K., 1998, Controlled Radical Polymerization, 10.1021/bk-1998-0685 · DOI · Paper page
  33. Huan K., 2001, J. Polym. Sci., Polym. Chem. Ed., 39, 1833, 10.1002/pola.1161 · DOI
  34. Asandei A. D., 2001, J. Polym. Sci., Polym. Chem. Ed., 39, 3392, 10.1002/pola.1322 · DOI
  35. Matyjaszewski K., 2000, Part A: Polym. Chem
  36. Hawker C. J., 2001, Chem. Rev., 101, 3661, 10.1021/cr990119u · DOI
  37. Benoit D., 1999, J. Am. Chem. Soc., 121, 3904, 10.1021/ja984013c · DOI
  38. Hawker C. J., 1994, J. Am. Chem. Soc., 116, 11185, 10.1021/ja00103a055 · DOI
  39. Pasquale A. J., 2001, Sci., Polym. Chem. Ed., 39, 216, 10.1002/1099-0518(20010101)39:1<216::AID-POLA240>3.0.CO;2-Z · DOI
  40. Mayadunne R. T. A., 2000, Macromolecules, 33, 243, 10.1021/ma991451a · DOI · Paper page
  41. Arduengo A. J., 1999, Tetrahedron, 55, 14523, 10.1016/S0040-4020(99)00927-8 · DOI
  42. Kuhn N., 1993, Synthesis, 561, 10.1055/s-1993-25902 · DOI
  43. Fuller J., 1997, J. Electrochem. Soc., 144, 3881, 10.1149/1.1838106 · DOI · Paper page
  44. Stetter H., 1974, Kuhlmann Angew. Chem., 86, 589, 10.1002/ange.19740861606 · DOI
  45. Breslow R., 1958, J. Am. Chem. Soc., 80, 3719, 10.1021/ja01547a064 · DOI
  46. Although, 1997, J. Liebigs Ann./Recl., 365
  47. For, 1997, J. Am. Chem. Soc., 119, 6674, 10.1021/ja970627q · DOI
  48. These, 2001, J. Am. Chem. Soc., 123, 9696, 10.1021/ja0165943 · DOI
  49. Arduengo A., 1999, J. Acc. Chem. Res., 32, 913, 10.1021/ar980126p · DOI
  50. Arduengo A. J., 1998, Chem. Z., 32, 6
  51. Bourissou D., 2000, Chem. Rev., 100, 39, 10.1021/cr940472u · DOI
  52. Herrmann W., 1997, Angew. Chem., Int. Ed. Engl., 36, 2162, 10.1002/anie.199721621 · DOI
  53. Scholl M., 1999, Tetrahedron Lett., 40, 2247, 10.1016/S0040-4039(99)00217-8 · DOI
  54. Huang J., 1999, J. Am. Chem. Soc., 121, 2674, 10.1021/ja9831352 · DOI · Paper page
  55. Weskamp T., 1998, Angew. Chem., Int. Ed., 37, 2490, 10.1002/(SICI)1521-3773(19981002)37:18<2490::AID-ANIE2490>3.0.CO;2-X · DOI
  56. Herrmann W. A., 1995, J. Angew. Chem., Int. Ed. Engl., 34, 2371, 10.1002/anie.199523711 · DOI
  57. Herrmann W. A., 1996, Angew. Chem., Int. Ed. Engl., 35, 2805, 10.1002/anie.199628051 · DOI
  58. Lappert M., 1988, J. Organomet. Chem., 358, 185, 10.1016/0022-328X(88)87079-7 · DOI
  59. Enders D., 1995, Angew. Chem., Int. Ed. Engl., 34, 1021, 10.1002/anie.199510211 · DOI · Paper page
  60. Arduengo A. J., 1997, J. Am. Chem. Soc., 119, 12742, 10.1021/ja973241o · DOI
  61. Arduengo A. J., 1995, J. Am. Chem. Soc., 117, 11027, 10.1021/ja00149a034 · DOI · Paper page
  62. Trnka T. M., 2001, Acc. Chem. Res., 34, 18, 10.1021/ar000114f · DOI
  63. Wanzlick H.-W., 1961, J Angew. Chem., 73, 493, 10.1002/ange.19610731408 · DOI
  64. Wanzlick H.-W., 1962, Angew. Chem., 74, 128
  65. Wanzlick H.-W., 1963, Chem. Ber., 96, 3024, 10.1002/cber.19630961127 · DOI
  66. Van Hummel G. J., 1982, Sect. B, 38, 1679, 10.1107/S0567740882006840 · DOI
  67. Gross R. A., 2001, Chem. Rev., 101, 2097, 10.1021/cr0002590 · DOI · Paper page
  68. (a) Lyman, D. J.; Rowland, S. M. Biomaterials.Encyclopedia ofPolymer Sciences and Engineering, 2nd ed.; 1985; Vol. 2, p 267.
  69. (b) Schindler, A.; Jeffcoat, R.; Kimmel, G. L.; Pitt, C. G.; Wall, M. E.; Zweidinger, R. InContemporary Topics in Polymer Science; Pearce, E. M., Schaefgen, J. R., Eds.; Plenum Press: New York, 1977; Vol. 2, p 251. · DOI
  70. Pett C. G., 1980, Controlled Release of Bioactive Materials
  71. Song C. X., 1987, Polym. J., 19, 485, 10.1295/polymj.19.485 · DOI
  72. Jacobs C., 1991, Macromolecules, 24, 3027, 10.1021/ma00011a001 · DOI
  73. Vanhoorne P., 1992, Macromolecules, 25, 37, 10.1021/ma00027a008 · DOI
  74. Kricheldorf H. R., 1985, Makromol. Chem., Suppl., 12, 25, 10.1002/macp.1985.020121985104 · DOI
  75. For, 1999, Chem. Rev., 100, 2071
  76. For, 2000, Chem. Commun., 1237
  77. For, 1995, Angew. Chem., Int. Ed. Engl., 34, 2698
  78. Boon J., 1986, J. Org. Chem., 51, 480, 10.1021/jo00354a013 · DOI · Paper page
  79. Adams C. J., 1998, Chem. Commun., 2097
  80. Cole A. C., J. Am. Chem. Soc., published on the web.
  81. Green L., 2000, Tetrahedron Lett., 41, 1343, 10.1016/S0040-4039(99)02289-3 · DOI
  82. Howarth J., 1997, Tetrahedron Lett., 38, 3097, 10.1016/S0040-4039(97)00554-6 · DOI
  83. Davis J. H., 1999, J. Tetrahedron Lett., 40, 1621, 10.1016/S0040-4039(99)00025-8 · DOI
  84. Fuller J., 1997, J. Electrochem. Soc., 144, 3881, 10.1149/1.1838106 · DOI · Paper page

Cited by

Metadata

Authors
Nyce, G. W., Glauser, T., Connor, E. F., Möck, A., Waymouth, R. M., & Hedrick, J. L.
Venue
Journal of the American Chemical Society
Publisher
American Chemical Society (ACS)
Published
2003-02-14
Volume
125
Issue
10
Pages
3046-3056
ISSN
  • 0002-7863 (ISSN-L)
  • 1520-5126
DOI
10.1021/ja021084+
OpenAlex
W2022854755
Cited by
301
References
1
FWCI
10.10
Type
journal article
Language
en
Open access
closed

About these checks

Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.

Statistics and arithmetic are recomputed, not judged.

Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.

What counts as a claim ›How we measure confidence ›How we check this ›

Are you an author, or do you see a problem with this page? Request a review

Data sources

Bibliographic data: Semantic Scholar, OpenAlex, Crossref.

Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).

Semantic Scholar’s data is described in: Kinney, R., et al. (2023). The Semantic Scholar Open Data Platform. arXiv:2301.10140.