Cited by 2,657

The DOI matches its Crossref record.

Visible light photocatalysis as a greener approach to photochemical synthesis

Yoon, Tehshik P., Ischay, Michael A., Du, Juana·2010·Nature Chemistry

Abstract

Light can be considered an ideal reagent for environmentally friendly, 'green' chemical synthesis; unlike many conventional reagents, light is non-toxic, generates no waste, and can be obtained from renewable sources. Nevertheless, the need for high-energy ultraviolet radiation in most organic photochemical processes has limited both the practicality and environmental benefits of photochemical synthesis on industrially relevant scales. This perspective describes recent approaches to the use of metal polypyridyl photocatalysts in synthetic organic transformations. Given the remarkable photophysical properties of these complexes, these new transformations, which use Ru(bpy)(3)(2+) and related photocatalysts, can be conducted using almost any source of visible light, including both store-bought fluorescent light bulbs and ambient sunlight. Transition metal photocatalysis thus represents a promising strategy towards the development of practical, scalable industrial processes with great environmental benefits.

Overview

Integrity signals

Registry

Crossref · 10.1038/nchem.687

Cites

Statistics

Recomputing p-values needs the paper’s full text.

Verification

Claims the paper makes

This paper’s full text isn’t openly available, so its claims and self-check weren’t run. The registry and citation checks still apply.

Claims other papers make about this one

Each is checked against this paper’s own text: does it say what the citing paper says it does?

Citations

Cites

No references could be resolved yet.

Research works printed but not linked: 46

  1. Morton, O. Silicon Valley sunrise. Nature 443, 19–22 (2006). · DOI
  2. Nocera, D. G. On the future of global energy. Daedalus 135, 112–115 (2006). · DOI
  3. Lewis, N. S. Toward cost-effective solar energy use. Science 315, 798–801 (2007). · DOI
  4. Roth, H. D. The beginnings of organic photochemistry. Angew. Chem. Int. Ed. Engl. 28, 1193–1207 (1989). · DOI
  5. Albini, A. & Fagnoni, M. Green chemistry and photochemistry were born at the same time. Green Chem. 6, 1–6 (2004). · DOI
  6. Albini, A. & Fagnoni, M. 1908: Giacomo Ciamician and the concept of green chemistry. ChemSusChem 1, 63–66 (2008). · DOI
  7. Ciamician, G. The photochemistry of the future. Science 36, 385–394 (1912). · DOI
  8. Fagnoni, M., Dondi, D., Ravelli, D. & Albini, A. Photocatalysis for the formation of the C–C bond. Chem. Rev. 107, 2725–2756 (2007). · DOI
  9. Protti, S. & Fagnoni, M. The sunny side of chemistry: Green synthesis by solar light. Photochem. Photobiol. Sci. 8, 1499–1516 (2009). · DOI
  10. Oelgemöller, M., Jung, C. & Mattay, J. Green photochemistry: Production of fine chemicals with sunlight. Pure Appl. Chem. 79, 1939–1947 (2007). · DOI
  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). · DOI
  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). · DOI
  13. Balzani, V., Credi, A. & Venturi, M. Photochemical conversion of solar energy. ChemSusChem 1, 26–58 (2008). · DOI
  14. Kalyanasundaram, K. Photophysics, photochemistry, and solar energy conversion with tris(bipyridyl)ruthenium(II) and its analogues. Coord. Chem. Rev. 46, 159–244 (1982). · DOI
  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). · DOI
  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). · DOI
  18. Nicewicz, D. A. & MacMillan, D. W. C. Merging photoredox catalysis with organocatalysis: The direct asymmetric alkylation of aldehydes. Science 3 22, 77–80 (2008). · DOI
  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). · DOI
  20. Cano-Yelo, H. & Deronzier, A. Photo-oxidation of some carbinols by the Ru(II) polypyridyl complex-aryl diazonium salt system. Tetrahedron Lett. 2 5, 5517–5520 (1984). · DOI
  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). · DOI
  22. Burstall, F. H. Optical activity dependent on co-ordinated bivalent ruthenium. J. Chem. Soc. 173–175 (1936). · DOI
  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). · DOI
  24. Kalyanasundaram, K., Kiwi, J. & Grätzel, M. Hydrogen evolution from water by visible light, a homogeneous three component test system for redox catalysis. Helv. Chim. Acta 61, 2720–2730 (1978). · DOI
  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). · DOI
  26. Crimmins, M. T. Synthetic applications of intramolecular enone-olefin photocycloadditions. Chem. Rev. 88, 1453–1473 (1988). · DOI
  27. Bach, T. Stereoselective intermolecular [2+2]-photocycloaddition reactions and their application in synthesis. Synthesis 683–708 (1998). · DOI
  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). · DOI
  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). · DOI
  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). · DOI
  31. Fournier, F. & Fournier, M. Transferts d'électrons assistés par les métaux de transition: influence de la nature du cation métallique sur la réduction de composés carbonylés en milieu aprotique. Can. J. Chem. 64, 881–890 (1986). · DOI
  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). · DOI
  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). · DOI
  34. MacMillan, D. W. C. The advent and development of organocatalysis. Nature 455, 304–308 (2008). · DOI
  35. Beeson, T. D., Mastracchio, A., Hong, J., Ashton, K. & MacMillan, D. W. C. Enantioselective organocatalysis using SOMO activation. Science 3 16, 582–585 (2007). · DOI · Paper page
  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). · DOI
  37. Slinker, J. D. et al. Efficient yellow electroluminescence from a single layer of a cyclometalated iridium complex. J. Am. Chem. Soc. 1 26, 2763–2767 (2004). · DOI
  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). · DOI
  39. Hagmann, W. K. The many roles for fluorine in medicinal chemistry. J. Med. Chem. 51, 4359–4369 (2008). · DOI · Paper page
  40. Purser, S., Moore, P. R., Swallow, S. & Gouverneur, V. Fluorine in medicinal chemistry. Chem. Soc. Rev. 37, 320–330 (2008). · DOI
  41. Zeitler, K. Photoredox catalysis with visible light. Angew. Chem. Int. Ed. 4 8, 9785–9789 (2009). · DOI
  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). · DOI
  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). · DOI
  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). · DOI
  45. Ferrere, S. & Gregg, B. A. Photosensitization of TiO2 by [FeII(2,2′-bipyridine-4,4′-dicarboxylic acid)2(CN)2]: Band selective electron injection from ultra-short-lived excited states. J. Am. Chem. Soc. 120, 843–844 (1998). · DOI
  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). · DOI

Cited by

Sorted by citations

See all 2,657

Metadata

Authors
Yoon, T. P., Ischay, M. A., & Du, J.
Venue
Nature Chemistry
Published
2010-06-23
Volume
2
Issue
7
Pages
527-532
ISSN
  • 1755-4330
  • 1755-4349
Cited by
2,657
References
0
Language
en

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

How to cite

Cite CoChat for the checks on this page, and the paper for its own findings.

This page
CoChat. (2026). Citation check: Visible light photocatalysis as a greener approach to photochemical synthesis. https://app.cochat.ai/papers/10.1038/nchem.687
The paper
Yoon, T. P., Ischay, M. A., & Du, J. (2010). Visible light photocatalysis as a greener approach to photochemical synthesis. Nature Chemistry. https://doi.org/10.1038/nchem.687