Light-induced hetero-diels-alder cycloaddition: A facile and selective photoclick reaction

Journal of the American Chemical Society

Volumn 133, Issue 14, 2011, Pages 5573-5579

  Arumugam, Selvanathan ^a   Popik, Vladimir V ^a  

^a UNIVERSITY OF GEORGIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2-NAPHTHOLS; AQUEOUS SOLUTIONS; DIELS-ALDER; DIELS-ALDER ADDUCT; ELECTRON-RICH; ENAMINES; HETERO-DIELS-ALDER; PHOTOLABELING; PHOTOSTABLE; QUANTITATIVE YIELDS; SPATIAL CONTROL; TIME-RESOLVED; VINYL ETHERS;

ETHERS; HYDRATION; METHANOL; OLEFINS; ORGANIC COMPOUNDS; PHENOLS; REACTION KINETICS; SOLUTIONS;

CYCLOADDITION;

CALCIFEDIOL; CHROMAN DERIVATIVE; ENAMINE; NAPHTHALENE DERIVATIVE;

ALDER; AQUEOUS SOLUTION; ARTICLE; CHEMICAL REACTION; CYCLOADDITION; HYDRATION; IRRADIATION; PHOTOAFFINITY LABELING; QUANTITATIVE ANALYSIS;

CHROMANS; CLICK CHEMISTRY; KINETICS; LIGHT; NAPHTHOQUINONES; PHOTOLYSIS;

EID: 79953674209     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja200356f     Document Type: Article

References (69)

1. Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2001, 40, 2004
2. Moses, J. E.; Moorhouse, A. D. Chem. Soc. Rev. 2007, 36, 1242
3. Nandivada, H.; Jiang, X.; Lahann, J. Adv. Mater. 2007, 19, 2197
4. Wu, P.; Feldman, A. K.; Nugent, A. K.; Hawker, C. J.; Scheel, A.; Voit, B.; Pyun, J.; Frechet, J. M. J.; Sharpless, K. B.; Fokin, V. V. Angew. Chem., Int. Ed. 2004, 43, 3928
5. Punna, S.; Kaltgrad, E.; Finn, M. G. Bioconjugate Chem. 2005, 16, 1536
6. Punna, S.; Kuzelka, J.; Wang, Q.; Finn, M. G. Angew. Chem., Int. Ed. 2005, 44, 2215
7. Johnson, J. A.; Lewis, D. R.; Diaz, D. D.; Finn, M. G.; Koberstein, J. T.; Turro, N. J. J. Am. Chem. Soc. 2006, 128, 6564
8. Thibault, R. J.; Takizawa, K.; Lowenheilm, P.; Helms, B.; Mynar, J. L.; Frechet, J. M. J.; Hawker, C. J. J. Am. Chem. Soc. 2006, 128, 12084
9. Joralemon, M. J.; OReilly, R. K.; Hawker, C. J.; Wooley, K. L. J. Am. Chem. Soc. 2005, 127 (16) 892
10. Malkoch, M.; Thibault, R. J.; Drockenmuller, E.; Messerschmidt, M.; Voit, B.; Russell, T. P.; Hawker, C. J. J. Am. Chem. Soc. 2005, 127, 14942
11. Tornoe, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057
12. Wang, Q.; Chan, T. R.; Hilgraf, R; Fokin, V V.; Sharpless, K. B.; Finn, M. G. J. Am. Chem. Soc. 2003, 125, 3192
13. Strable, E.; Prasuhn, D. E., Jr.; Udit, A. K.; Brown, S.; Link, A. J.; Ngo, J. T.; Lander, G.; Quispe, J.; Potter, C. S.; Carragher, B.; Tirrell, D. A.; Finn, M. G. Bioconjugate Chem. 2008, 19, 866
14. von Maltzahn, G.; Ren, Y.; Park, J.-H.; Min, D.-H.; Kotamraju, V. R.; Jayakumar, J.; Fogal, V.; Sailor, M. J.; Ruoslahti, E.; Bhatia, S. N. Bioconjugate Chem. 2008, 19, 1570
15. Kolb, H. C.; Sharpless, K. B. Drug Discovery Today 2003, 8, 1128
16. Sharpless, K. B.; Manetsch, R. Expert Opin. Drug Discovery 2006, 1, 525
17. Gaetke, L. M.; Chow, C. K. Toxicology 2003, 189, 147
18. Gierlich, J.; Burley, G. A.; Gramlich, P. M. E.; Hammond, D. M.; Carell, T. Org. Lett. 2006, 8, 3639
19. Burrows, C. J.; Muller, J. G. Chem. Rev. 1998, 98, 1109
20. Kamphuis, M. M. J.; Johnston, A. P. R.; Such, G. K.; Dam, H. H.; Evans, R. A.; Scott, A. M.; Nice, E. C.; Heath, J. K.; Caruso, F. J. Am. Chem. Soc. 2010, 132, 15881
21. Wang, Q.; Chan, T. R.; Hilgraf, R.; Fokin, V. V.; Sharpless, K. B.; Finn, M. G. J. Am. Chem. Soc. 2003, 125, 3192
22. Waengler, C.; Schirrmacher, R.; Bartenstein, P.; Waengler, B. Curr. Med. Chem. 2010, 17, 1092
23. Bernardin, A.; Cazet, A. l.; Guyon, L.; Delannoy, P.; Vinet, F.; Bonnaffé, D.; Texier, I. Bioconjugate Chem. 2010, 21, 583
24. Baskin, J. M.; Prescher, J. A.; Laughlin, S. T.; Agard, N. J.; Chang, P. V.; Miller, I. A.; Lo, A.; Codelli, J. A.; Bertozzi, C. R. Proc. Natl. Acad. Sci. U.S.A. 2007, 104, 16793
25. Sletten, E. M.; Bertozzi, C. R. Org. Lett. 2008, 10, 3097
26. Codelli, J. A.; Baskin, J. M.; Agard, N. J.; Bertozzi, C. R. J. Am. Chem. Soc. 2008, 130, 11486
27. Ning, X.; Guo, J.; Wolfert, M. A.; Boons, G.-J. Angew. Chem., Int. Ed. 2008, 47, 2253
28. Debets, M. F.; Berkel, S. S. v.; Schoffelen, S.; Rutjes, F. P. J. T.; Hest, J. C. M. v.; Delft, F. L. v. Chem. Commun. 2010, 46, 97
29. Palomo, J. M. Eur. J. Org. Chem. 2010, 6303
30. Ramachary, D. B.; Barbas, C. F. Chem.-Eur. J. 2004, 10, 5323
31. Nandivada, H.; Jiang, X.; Lahann, J. Adv. Mater. 2007, 19, 2197
32. Durmaz, H.; Colakoglu, B.; Tunca, U.; Hizal, G. J. Polym. Sci., Part A: Polym. Chem. 2006, 44, 1667
33. Dag, A.; Durmaz, H.; Hizal, G.; Tunca, U. J. Polym. Sci., Part A: Polym. Chem. 2008, 46, 302
34. Gacal, B.; Durmaz, H.; Tasdelen, M. A.; Hizal, G.; Tunca, U.; Yagci, Y.; Demirel, A. L. Macromolecules 2006, 39, 5330
35. Delgado, J. L.; de la Cruz, P.; Langa, F.; Urbina, A.; Casado, J.; Lopez Navarrete, J. T. Chem. Commun. 2004, 1734
36. Latham-Timmons, H. A.; Wolter, A.; Roach, J. S.; Giare, R.; Leuck, M. Nucleosides, Nucleotides Nucleic Acids 2003, 22, 1495
37. Sun, X.-L.; Stabler, C. L.; Cazalis, C. S.; Chaikof, E. L. Bioconjugate Chem. 2006, 17, 52
38. Proupin-Perez, M.; Cosstick, R.; Liz-Marzan, L. M.; Salgueirino-Maceira, V.; Brust, M. Nucleosides, Nucleotides Nucleic Acids 2005, 24, 1075
39. Yousaf, M. N.; Houseman, B. T.; Mrksich, M. Proc. Natl. Acad. Sci. U.S.A. 2001, 98, 5992
40. Dillmore, W. S.; Yousaf, M. N.; Mrksich, M. Langmuir 2004, 20, 7223
41. Rusmini, F.; Zhong, Z.; Feijen, J. Biomacromolecules 2007, 3, 1775
42. Seelig, B.; Jaschke, A. Tetrahedron Lett. 1997, 38, 7729
43. Graham, D.; Enright, A. Curr. Org. Synth. 2006, 3, 9
44. Pozsgay, V.; Vieira, N. E.; Yergey, A. Org. Lett. 2002, 4, 3191
45. Van den Berg, R. J. B. H. N.; Noort, D.; Milder-Enacache, E. S.; Van der Marel, G. A.; Van Boom, J. H.; Benschop, H. P. Eur. J. Org. Chem. 1999, 2593
46. Peeters, C. C. A. M.; Lagerman, P. R.; de Weers, O.; Oomen, L. A.; Hoogerhout, P.; Beurret, M.; Poolman, J. T. Polysaccharide-Conjugate Vaccines. In Vaccine Protocols; Robinson, A.; Farrar, G.; Wiblin, C., Eds.; Humana Press, Inc.: Totowa, NJ, 1996; p 111.
47. Methods in Enzymology; Academic Press: San Diego, CA, 1994; Vol 242.
48. Neoglycoconjugates. Preparation and Applications; Lee, Y. C.; Lee, R. T., Eds.; Academic Press: New York, 1994; p 325.
49. Robbins, J. B.; Schneerson, R.; Anderson, P.; Smith, D. H. J. Am. Med. Assoc. 1996, 276, 1181
50. Seelig, B.; Jaschke, A. Chem. Biol. 1999, 6, 167
51. Husar, G. M.; Anziano, D. J.; Leuck, M.; Sebesta, D. P. Nucleosides, Nucleotides Nucleic Acids 2001, 20, 559
52. Segura, J. L.; Martin, N. Chem. Rev. 1999, 11, 3199
53. Martin, N.; Seoane, C.; Hanack, M. Org. Prep. Proc. Int 1991, 23, 237
54. Oppolzer, W. Synthesis 1978, 793
55. Wang, Y; Song, W.; Hu, W. J.; Lin, Q. Angew. Chem., Int. Ed. 2009, 48, 5330
56. Song, W.; Wang, Y.; Qu, J.; MAdden, M. M.; Lin, Q. Angew. Chem., Int. Ed. 2008, 47, 2832
57. De Forest, C. A.; Polizzotti, B. D.; Anseth, K. S. Nat. Mater. 2009, 8, 659
58. Fiore, M.; Marra, A.; Dondoni, A. J. Org. Chem. 2009, 74, 4422
59. Fiore, M.; Chambery, A.; Marra, A.; Dondoni, A. Org. Biomol. Chem. 2009, 7, 3910
60. Killops, K. L; Campos, L. M.; Hawker, C. J. J. Am. Chem. Soc. 2008, 130, 5062
61. Campos, L. M.; Killops, K. L.; Sakai, R.; Paulusse, J. M. J.; Damiron, D.; Drockenmuller, E.; Messmore, B. W.; Hawker, C. J. Macromolecules 2008, 41, 7063
62. Chan, J. W.; Yu, B.; Hoyle, C. E.; Lowe, A. B. Chem. Commun. 2008, 4959
63. Hensarling,Ryan, M.; Doughty,Vanessa, A.; Chan,Justin, W.; Patton Derek, L. J. Am. Chem. Soc. 2009, 131, 14673
64. Arumugam, S.; Popik, V. V. J. Am. Chem. Soc. 2009, 131, 11892
65. See Supporting Information.
66. Quinone Methides; Rokita, S. E., Ed.; Wiley: Hoboken, 2009, and references cited therein.
67. Itoh, T. Prog. Polym. Sci. 2001, 26, 1019
68. Dolenc, J.; Sket, B.; Strlic, M. Tetrahedron Lett. 2002, 43, 5669
69. Rokita, S. E. Reversible Alkylation of DNA by Quinone Methides. In Quinone Methides; Rokita, S. E., Ed.; Wiley: Hoboken, 2009; p 297.