Erratum: Benzimidazole and related ligands for cu-catalyzed azide-alkyne cycloaddition (Journal of the American Chemical Society (2007) 129: 42 (12696-12704) DOI: 10.1021/ja072678l);Benzimidazole and related ligands for Cu-catalyzed azide-alkyne cycloaddition

Journal of the American Chemical Society

Volumn 129, Issue 42, 2007, Pages 12696-12704

  Rodionov, Valentin O ^a   Presolski, Stanislav I ^a   Gardinier, Sean ^a   Lim, Yeon Hee ^a   Finn, M G ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE; CATALYST ACTIVITY; CONCENTRATION (PROCESS); CYCLOADDITION; PH; SUBSTITUTION REACTIONS;

ALKYLCARBOXYLATE; BENZIMIDAZOLE-BASED LIGANDS; CYCLOADDITION REACTION; RATE MEASUREMENTS;

LIGANDS;

ALKYNE DERIVATIVE; AZIDE; BENZIMIDAZOLE; BENZIMIDAZOLE DERIVATIVE; BENZOTHIAZOLE DERIVATIVE; COPPER; TRIAZOLE DERIVATIVE;

ARTICLE; CALORIMETRY; CATALYSIS; CATALYST; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLOADDITION;

EID: 35548971206     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja400176a     Document Type: Erratum

References (47)

1. Tornøe, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057-3062.
2. Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2596-2599.
3. More than 600 articles have been published describing the use of the CuAAC process since its discovery; the particular examples cited here are therefore intended to be illustrative rather than comprehensive.
4. Gupta, S. S.; Kuzelka, J.; Singh, P.; Lewis, W. G.; Manchester, M.; Finn, M. G. Bioconjugate Chem. 2005, 16, 1572-1579.
5. Dirks, A. J.; Van Berkel, S. S.; Hatzakis, N. S.; Opsteen, J. A.; van Delft, F. L.; Cornelissen, J. J. L. M.; Rowan, A. E.; van Hest, J. C. M.; Rutjes, F. P. J. T.; Nolte, R. J. M. Chem. Commun. 2005, 4172-4174.
6. Link, A. J.; Tirrell, D. A. J. Am. Chem. Soc. 2003, 125, 11164-11165.
7. Speers, A. E.; Cravatt, B. F. Chem. Biol. 2004, 11, 535-546.
8. Beatty, K. E.; Xie, F.; Wang, Q.; Tirrell, D. A. J. Am. Chem. Soc. 2005, 127, 14150-14151.
9. Sieber, S. A.; Niessen, S.; Hoover, H. S.; Cravatt, B. F. Nat. Chem. Biol. 2006, 2, 274-281.
10. Wu, P.; Malkoch, M.; Hunt, J.; Vestberg, R.; Kaltgrad, E.; Finn, M. G.; Fokin, V. V.; Sharpless, K. B.; Hawker, C. J. Chem. Commun. 2005, 5775-5777.
11. Malkoch, M.; Schleicher, K.; Drockenmuller, E.; Hawker, C. J.; Russell, T. P.; Wu, P.; Fokin, V. V. Macromolecules 2005, 38, 3663-3678.
12. Gupta, S. S.; Raja, K. S.; Kaltgrad, E.; Strahle, E.; Finn, M. G. Chem. Commun. 2005, 4315-4317.
13. Parrish, B.; Breitenkamp, R. B.; Emrick, T. J. Am. Chem. Soc. 2005, 127, 7404-7410.
14. Opsteen, J. A.; van Hest, J. C. M. Chem. Commun. 2005, 57-59.
15. Binder, W. H.; Kluger, C. Macromolecules 2004, 37, 9321-9330.
16. Sumerlin, B. S.; Tsarevsky, N. V.; Louche, G.; Lee, R. Y.; Matyjaszewski, K. Macromolecules 2005, 38, 7540-7545.
17. Fazio, F.; Bryan, M. C.; Blixt, O.; Paulson, J. C.; Wong, C.-H. J. Am. Chem. Soc. 2002, 124, 14397-14402.
18. Goess, B. C.; Hannoush, R. N.; Chan, L. K.; Kirchhausen, T.; Shair, M. D. J. Am. Chem. Soc. 2006, 128, 5391-5403.
19. Díaz, D. D.; Punna, S.; Holzer, P.; McPherson, A. K.; Sharpless, K. B.; Fokin, V. V.; Finn, M. G. J. Polym. Sci., Part A: Polym. Chem. 2004, 42, 4392-4403.
20. Meng, J.-C.; Averbuj, C.; Lewis, W. G.; Siuzdak, G.; Finn, M. G. Angew. Chem., Int. Ed. 2004, 43, 1255-1260.
21. Collman, J. P.; Devaraj, N. K.; Chidsey, C. E. D. Langmuir 2004, 20, 1051-1053.
22. Lummerstorfer, T.; Hoffmann, H. J. Phys. Chem. B 2004, 108, 39663-33966.
23. Devaraj, N. K.; Miller, G. P.; Ebina, W.; Kakaradov, B.; Collman, J. P.; Kool, E. T.; Chidsey, C. E. D. J. Am. Chem. Soc. 2005, 127, 8600-8601.
24. Huisgen, R. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; Wiley: New York, 1984; Vol. 1, pp 1-176.
25. Chan, T. R.; Hilgraf, R.; Sharpless, K. B.; Fokin, V. V. Org. Lett. 2004, 6, 2853-2855.
26. Thompson, L. K.; Ramaswamy, B. S.; Seymour, E. A. Can. J. Chem. 1977, 55, 878-888.
27. Blackman, A. G. Polyhedron 2004, 24, 1-39.
28. Su, C.-Y.; Kang, B.-S.; Wen, T.-B.; Tong, Y.-X.; Yang, X.-P.; Zhang, C.; Liu, H.-Q.; Sun, J. Polyhedron 1999, 18, 1577-1585.
29. Su, C.-Y.; Yang, X.-P.; Kang, B.-S.; Mak, T. C. W. Angew. Chem., Int. Ed. 2001, 40, 1725-1728.
30. Rodionov, V. O.; Fokin, V. V.; Finn, M. G. Angew. Chem., Int. Ed. 2005, 44, 2210-2215.
31. Hendriks, H. M. J.; Birker, P. J. M. W. L.; van Rijn, J.; Verschoor, G. C.; Reedijk, J. J. Am. Chem. Soc. 1982, 104, 3607-3617.
32. Lewis, W. G.; Magallon, F. G.; Fokin, V. V.; Finn, M. G. J. Am. Chem. Soc. 2004, 126, 9152-9153.
33. Sokolowska, M.; Bal, W. J. Inorg. Biochem. 2005, 99, 1653-1660.
34. Hegetschweiler, K.; Saltman, P. Inorg. Chem. 1986, 25, 107-109.
35. Meng, J.-C.; Fokin, V. V.; Finn, M. G. Tetrahedron Lett. 2005, 46, 4543-4546.
36. LeBlond, C.; Wang, J.; Larsen, R. D.; Orella, C. J.; Forman, A. L.; Landau, R. N.; Laquidara, J.; Sowa, J. R.; Blackmond, D. G.; Sun, Y. K. Thermochim. Acta 1996, 289, 189-207.
37. Blackmond, D. G.; Rosner, T.; Pfaltz, A. Org. Process Res. Dev. 1999, 3, 275-280.
38. Singh, U. K.; Strieter, E. R.; Blackmond, D. G.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 14104-14114.
39. Mathew, J. S.; Klussmann, M.; Iwamura, H.; Valera, F.; Futran, A.; Emanuelsson, E. A. C.; Blackmond, D. G. J. Org. Chem. 2006, 71, 4711-4722.
40. Díez-González, S.; Correa, A.; Cavallo, L.; Nolan, S. P. Chem. - Eur. J. 2006, 12, 7558-7564.
41. Tanaka, K.; Kageyama, C.; Fukase, K. Tetrahedron Lett. 2007, 48, 6475-6479.
42. Not discussed here are related series of tris(oxazolinylmethyl)amine ligands, which we have found in preliminary studies to give catalysts of comparable efficiency to tris(triazolylmethyl)amines. The attempted use of these systems in chiral kinetic resolution and desymmetrization reactions will be described elsewhere.
43. Thompson, L. K.; Ramaswamy, B. S.; Seymour, E. A. Can. J. Chem. 1977, 55, 878-888.
44. Birker, P. J. M. W. L.; Hendriks, H. M. J.; Reedijk, J.; Verschoor, G. C. Inorg. Chem. 1981, 20, 2408-2414.
45. Zakrzewski, A.; Janota, H. Pestycydy (Warsaw) 2004, 31-38.
46. Vetelino, M. G.; Coe, J. W. Tetrahedron Lett. 1994, 35, 219-222.
47. Ichikawa, K.; Nakata, K.; Ibrahim, M. M. Chem. Lett. 2000, 796-797.