Copper catalyst activation driven by photoinduced electron transfer: A prototype photolatent click catalyst

Angewandte Chemie - International Edition

Volumn 51, Issue 29, 2012, Pages 7137-7141

  Harmand, Lydie ^a   Cadet, Sarah ^a   Kauffmann, Brice ^b   Scarpantonio, Luca ^a   Batat, Pinar ^a   Jonusauskas, Gediminas ^a   McClenaghan, Nathan D ^a   Lastécouères, Dominique ^a   Vincent, Jean Marc ^a  

^a UNIVERSITÉ DE BORDEAUX   (France)

^b INSTITUT EUROPÉEN DE CHIMIE ET BIOLOGIE   (France)

Author keywords

Click chemistry; Copper; Huisgen cycloaddition; Photocontrolled catalysts; Photolatent catalysts

Indexed keywords

CLICK CHEMISTRY; COPPER CATALYST; HUISGEN CYCLOADDITION; LIGHT IRRADIATIONS; PHOTO-INDUCED ELECTRON TRANSFER; PHOTOLATENT CATALYST; PRECATALYSTS; REACTION MEDIUM; ROOM TEMPERATURE;

COPPER; IRRADIATION; METHANOL;

CATALYSTS;

EID: 84863845582     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201203014     Document Type: Article

References (48)

1. For a recent review on photocontrolled catalysts, see:, R. S. Stoll, S. Hecht, Angew. Chem. 2010, 122, 5176-5200
2. Angew. Chem. Int. Ed. 2010, 49, 5054-5075.
3. For selected examples, see
4. B. K. Keitz, R. H. Grubbs, J. Am. Chem. Soc. 2009, 131, 2038-2039
5. D. Wang, K. Wurst, W. Knolle, U. Decker, L. Prager, S. Naumov, M. R. Buchmeiser, Angew. Chem. 2008, 120, 3311-3314
6. Angew. Chem. Int. Ed. 2008, 47, 3267-3270
7. L. Delaude, M. Szypa, A. Demonceau, A. F. Noels, Adv. Synth. Catal. 2002, 344, 749-756
8. A. Fürstner, L. Ackermann, Chem. Commun. 1999, 95-96
9. M. Picquet, C. Bruneau, P. H. Dixneuf, Chem. Commun. 1998, 2249-2250
10. A. Hafner, A. Mülhebach, P. A. van der Schaaf, Angew. Chem. 1997, 109, 2113-2116
11. Angew. Chem. Int. Ed. Engl. 1997, 36, 2121-2124
12. A. L. Prignano, W. C. Trogler, J. Am. Chem. Soc. 1987, 109, 3586-3595
13. J. C. Mitchener, M. S. Wrighton, J. Am. Chem. Soc. 1981, 103, 975-977.
14. H. Sugimoto, T. Kimura, S. Inoue, J. Am. Chem. Soc. 1999, 121, 2325-2326.
15. V. V. Rostovtsev, L. G. Green, V. V. Fokin, K. B. Sharpless, Angew. Chem. 2002, 114, 2708-2711
16. Angew. Chem. Int. Ed. 2002, 41, 2596-2599
17. C. W. Torne, C. Christensen, M. Meldal, J. Org. Chem. 2002, 67, 3057-3064.
18. See the themed issues
19. "Applications of click chemistry", guest Eds.: M. G. Finn, V. Fokin, Chem. Soc. Rev. 2010, 39, 1231-1405
20. "Click chemistry in polymer science", guest Ed.: W. H. Binder, Macromol. Rapid Commun. 2008, 29, 943-1185.
21. For selected reviews, see
22. M. Meldal, C. W. Torne, Chem. Rev. 2008, 108, 2952-3015
23. V. D. Bock, H. Hiemstra, J. H. van Maarseveen, Eur. J. Org. Chem. 2006, 51-68
24. L. Liang, D. Astruc, Coord. Chem. Rev. 2011, 255, 2933-2945.
25. For a review focusing on copper(I) click catalysts, see:, S. Díez-González, Catal. Sci. Technol. 2011, 1, 166-178.
26. S. Díez-González, E. D. Stevens, S. P. Nolan, Chem. Commun. 2008, 4747-4749.
27. Y. L. Chow, G. E. Buono-Core, Can. J. Chem. 1983, 61, 795-800
28. Y. L. Chow, G. E. Buono-Core, Can. J. Chem. 1983, 61, 801-808
29. Y. L. Chow, G. E. Buono-Core, J. Am. Chem. Soc. 1982, 104, 3770-3771
30. Y. L. Chow, G. E. Buono-Core, J. Am. Chem. Soc. 1986, 108, 1234-1239.
31. Y. L. Chow, G. E. Buono-Core, C. W. B. Lee, J. C. Scaiano, J. Am. Chem. Soc. 1986, 108, 7620-7627
32. Y. L. Chow, G. E. Buono-Core, J. Chem. Soc. Chem. Commun. 1985, 592-594.
33. G. E. Buono-Core, A. H. Klahn, F. Aros, V. Astorga, Polyhedron 1996, 15, 363-366
34. G. E. Buono-Core, A. H. Klahn, C. Bahamondes, F. Aros, M. Tejos, V. Astorga, Inorg. Chim. Acta 1997, 257, 241-245.
35. N. Candelon, D. Lastécouères, A. Khadri Diallo, J. Ruiz Aranzaes, D. Astruc, J.-M. Vincent, Chem. Commun. 2008, 41-43
36. L. Harmand, M.-H. Lescure, N. Candelon, M. Duttine, D. Lastécouères, J.-M. Vincent, Tetrahedron Lett. 2012, 53, 1417-1420.
37. P. L. Golas, N. V. Tsarevsky, B. S. Sumerlin, K. Matyjaszewski, Macromolecules 2006, 39, 6451-6457
38. L. Liang, J. Ruiz, D. Astruc, Adv. Synth. Catal. 2011, 353, 3434-3450.
39. C. Capello, U. Fischer, K. Hungerbühler, Green Chem. 2007, 9, 927-934.
40. M. Montalti, A. Credi, L. Prodi, M. T. Gandolfi, in Handbook of Photochemistry, 3 rd ed., CRC Press, New York, 2006, pp. 601-604.
41. I. Carmichael, G. L. Hug, J. Phys. Chem. Ref. Data 1986, 15, 1-250.
42. G. Cosa, L. J. Martinez, J. C. Scaiano, Phys. Chem. Chem. Phys. 1999, 1, 3533-3537.
43. D. Rehm, A. Weller, Isr. J. Chem. 1970, 8, 259-271.
44. T. V. Popova, N. V. Aksenova, Russ. J. Coord. Chem. 2003, 29, 743-765.
45. L. Amankwa, L. G. Chatten, Analyst 1984, 109, 57-60
46. D. W. Margerum, L. F. Wong, F. P. Bossu, K. L. Chellappa, J. J. Czarnecki, S. T. Kirksey, Jr., T. A. Neubecker, in Bioinorganic Chemistry II, Vol. 162, Advances in Chemistry Series, ACS, 1977, pp. 281-303.
47. S. Lal, S. Díez-González, J. Org. Chem. 2011, 76, 2367-2373.
48. C. Shao, G. Cheng, D. Su, J. Xu, X. Wang, Y. Hu, Adv. Synth. Catal. 2010, 352, 1587-1592.