Visible light photocatalysis as a greener approach to photochemical synthesis

Nature Chemistry

Volumn 2, Issue 7, 2010, Pages 527-532

  Yoon, Tehshik P ^a   Ischay, Michael A ^a   Du, Juana ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOMETALLIC COMPOUND; TRANSITION ELEMENT; TRIS(2,2' BIPYRIDYL)RUTHENIUM(II); TRIS(2,2'-BIPYRIDYL)RUTHENIUM(II);

ARTICLE; CATALYSIS; CHEMISTRY; LIGHT; OXIDATION REDUCTION REACTION; PHOTOCHEMISTRY;

CATALYSIS; LIGHT; ORGANOMETALLIC COMPOUNDS; OXIDATION-REDUCTION; PHOTOCHEMICAL PROCESSES; TRANSITION ELEMENTS;

EID: 77953990194     PISSN: 17554330     EISSN: 17554349     Source Type: Journal    
DOI: 10.1038/nchem.687     Document Type: Article

References (46)

1. Morton, O. Silicon Valley sunrise. Nature 443, 19-22 (2006).
2. Nocera, D. G. On the future of global energy. Daedalus 135, 112-115 (2006).
3. Lewis, N. S. Toward cost-effective solar energy use. Science 315, 798-801 (2007).
4. Roth, H. D. The beginnings of organic photochemistry. Angew. Chem. Int. Ed. Engl. 28, 1193-1207 (1989).
5. Albini, A. & Fagnoni, M. Green chemistry and photochemistry were born at the same time. Green Chem. 6, 1-6 (2004).
6. Albini, A. & Fagnoni, M. 1908: Giacomo Ciamician and the concept of green chemistry. ChemSusChem 1, 63-66 (2008).
7. Ciamician, G. The photochemistry of the future. Science 36, 385-394 (1912).
8. Fagnoni, M., Dondi, D., Ravelli, D. & Albini, A. Photocatalysis for the formation of the C-C bond. Chem. Rev. 107, 2725-2756 (2007).
9. Protti, S. & Fagnoni, M. The sunny side of chemistry: Green synthesis by solar light. Photochem. Photobiol. Sci. 8, 1499-1516 (2009).
10. Oelgemoller, M., Jung, C. & Mattay, J. Green photochemistry: Production of fine chemicals with sunlight. Pure Appl. Chem. 79, 1939-1947 (2007).
11. Esser, P., Pohlmann, B. & Scharf, H.-D. The photochemical synthesis of fine chemicals with sunlight. Angew. Chem. Int. Ed. Engl. 33, 2009-2023 (1994).
12. Lewis, N. S. & Nocera, D. G. Powering the planet: Chemical challenges in solar energy utilization. Proc. Natl Acad. Sci. USA 103, 15729-15735 (2006).
13. Balzani, V., Credi, A. & Venturi, M. Photochemical conversion of solar energy. ChemSusChem 1, 26-58 (2008).
14. Kalyanasundaram, K. Photophysics, photochemistry, and solar energy conversion with tris(bipyridyl)ruthenium(II) and its analogues. Coord. Chem. Rev. 46, 159-244 (1982).
15. Juris, A., Balzani, V., Barigelletti, F., Campagna, S., Belser, P. & von Zelewsky, A. Ru(II) polypyridine complexes: Photophysics, photochemistry, electrochemistry, and chemiluminescence. Coord. Chem. Rev. 84, 85-277 (1988).
16. Kalyanasundaram, K. in Photochemistry of Polypyridine and Porphyrin Complexes 339-368 (Academic Press, 1992).
17. Ischay, M. A., Anzovino, M. E., Du, J. & Yoon, T. P. Efficient visible light photocatalysis of [2+2] enone cycloadditions. J. Am. Chem. Soc. 130, 12886-12887 (2008).
18. Nicewicz, D. A. & MacMillan, D. W. C. Merging photoredox catalysis with organocatalysis: The direct asymmetric alkylation of aldehydes. Science 322, 77-80 (2008).
19. Cano-Yelo, H. & Deronzier, A. Photocatalysis of the Pschorr reaction by tris- (2,2'-bipyridyl)ruthenium(II) in the phenanthrene series. J. Chem. Soc. Perkin Trans. 2 1093-1098 (1984).
20. Cano-Yelo, H. & Deronzier, A. Photo-oxidation of some carbinols by the Ru(II) polypyridyl complex-aryl diazonium salt system. Tetrahedron Lett. 25, 5517-5520 (1984).
21. Zen, J.-M., Liou, S.-L., Kumar, A. S. & Hsia, M.-S. An efficient and selective photocatalytic system for the oxidation of sulfides to sulfoxides. Angew. Chem. Int. Ed. 42, 577-579 (2003).
22. Burstall, F. H. Optical activity dependent on co-ordinated bivalent ruthenium. J. Chem. Soc. 173-175 (1936).
23. Demas, J. N. & Crosby, G. A. Quantum efficiencies on transition metal complexes. II. Charge-transfer luminescence. J. Am. Chem. Soc. 93, 2841-2847 (1971).
24. Kalyanasundaram, K., Kiwi, J. & Gratzel, M. Hydrogen evolution from water by visible light, a homogeneous three component test system for redox catalysis. Helv. Chim. Acta 61, 2720-2730 (1978).
25. Brown, G. M., Brunschwig, B. S., Creutz, C., Endicott, J. F. & Sutin, N. Homogeneous catalysis of the photoreduction of water by visible light. Mediation by a tris(2,2×-bipyridine)ruthenium(II)-cobalt(II) macrocycle system. J. Am. Chem. Soc. 101, 1298-1300 (1979).
26. Crimmins, M. T. Synthetic applications of intramolecular enone-olefin photocycloadditions. Chem. Rev. 88, 1453-1473 (1988).
27. Bach, T. Stereoselective intermolecular [2+2]-photocycloaddition reactions and their application in synthesis. Synthesis 683-708 (1998).
28. Baik, T.-G., Luiz, A. L., Wang, L.-C. & Krische, M. J. A diastereoselective metal-catalyzed [2+2] cycloaddition of bis-enones. J. Am. Chem. Soc. 123, 6716-6717 (2001).
29. Roh, Y., Jang, H.-Y., Lynch, V., Bauld, N. L. & Krische, M. J. Anion radical chain cycloaddition of tethered enones: Intramolecular cyclobutanation and Diels-Alder cycloaddition. Org. Lett. 4, 611-613 (2002).
30. Yang, J., Felton, G. A. N., Bauld, N. L. & Krische, M. J. chemically induced anion radical cycloadditions: Intramolecular cyclobutanation of bis(enones) via homogeneous electron transfer. J. Am. Chem. Soc. 126, 1634-1635 (2004).
31. Fournier, F. & Fournier, M. Transferts d'electrons assistes par les metaux de transition: influence de la nature du cation metallique sur la reduction de composes carbonyles en milieu aprotique. Can. J. Chem. 64, 881-890 (1986).
32. House, H. O., Huber, L. E. & Umen, M. J. Empirical rules for estimating the reduction potential of α, β-unsaturated carbonyl compounds. J. Am. Chem. Soc. 94, 8471-8475 (1972).
33. Du, J. & Yoon, T. P. Crossed intermolecular [2+2] cycloadditions of acyclic enones via visible light photocatalysis. J. Am. Chem. Soc. 131, 14604-14605 (2009).
34. MacMillan, D. W. C. The advent and development of organocatalysis. Nature 455, 304-308 (2008).
35. Beeson, T. D., Mastracchio, A., Hong, J., Ashton, K. & MacMillan, D. W. C. Enantioselective organocatalysis using SOMO activation. Science 316, 582-585 (2007).
36. Nagib, D. A., Scott, M. E. & MacMillan, D. W. C. Enantioselective α-trifluoromethylation of aldehydes via photoredox organocatalysis. J. Am. Chem. Soc. 131, 10875-10877 (2009).
37. Slinker, J. D. et al. Efficient yellow electroluminescence from a single layer of a cyclometalated iridium complex. J. Am. Chem. Soc. 126, 2763-2767 (2004).
38. Flamigni, L., Barbieri, A., Sabatini, C., Ventura, B. & Barigelletti, F. Photochemistry and photophysics of coordination compounds: Iridium. Top. Curr. Chem. 281, 143-203 (2007).
39. Hagmann, W. K. The many roles for fluorine in medicinal chemistry. J. Med. Chem. 51, 4359-4369 (2008).
40. Purser, S., Moore, P. R., Swallow, S. & Gouverneur, V. Fluorine in medicinal chemistry. Chem. Soc. Rev. 37, 320-330 (2008).
41. Zeitler, K. Photoredox catalysis with visible light. Angew. Chem. Int. Ed. 48, 9785-9789 (2009).
42. Narayanam, J. M. R., Tucker, J. W. & Stephenson, C. R. J. Electron-transfer photoredox catalysis: Development of a tin-free reductive dehalogenation reaction. J. Am. Chem. Soc. 131, 8756-8757 (2009).
43. Tucker, J. W., Narayanam, J. M. R., Krabbe, S. W. & Stephenson, C. R. J. Electron transfer photoredox catalysis: Intramolecular radical addition to indoles and pyrroles. Org. Lett. 12, 368-371 (2010).
44. Koike, T. & Akita, M. Photoinduced oxyamination of enamines and aldehydes with TEMPO catalyzed by [Ru(bpy)3]2+. Chem. Lett. 38, 166-167 (2009).
45. 2]: Band selective electron injection from ultrashort- lived excited states. J. Am. Chem. Soc. 120, 843-844 (1998).
46. Green, O., Gandhi, B. A. & Burstyn, J. N. Photophysical characteristics and reactivity of bis(2,9-di-tert-butyl-1,10-phenanthroline) copper(I). Inorg. Chem. 48, 5704-5714 (2009).