Preparation of organic compounds using photocatalytic reactions

Current Organic Chemistry

Volumn 17, Issue , 2013, Pages 2459-2481

  Vorontsov, Alexander V ^a,b   Arsentyev, Alexey V ^a,b  

^a BORESKOV INSTITUTE OF CATALYSIS   (Russian Federation)

^b NOVOSIBIRSK STATE UNIVERSITY   (Russian Federation)

Author keywords

Electron transfer; Energy transfer; Hydrogen abstraction; Sensitized reactions; Sensitizer; Singlet oxygen; Synthesis; Visible light

Indexed keywords

CHEMICAL BONDS; ENERGY TRANSFER; INDUSTRIAL RESEARCH; OXYGEN;

ELECTRON TRANSFER; ENERGY-TRANSFER; HYDROGEN ABSTRACTION; ORGANIC REACTION; PHOTOCATALYTIC REACTIONS; SENSITISER; SENSITIZED REACTION; SINGLET OXYGEN; STATE OF THE ART; VISIBLE LIGHT;

PHOTOCATALYSIS;

EID: 84937644668     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/13852728113179990060     Document Type: Article

References (160)

1. Maity, S.; Zheng, N. A Photo Touch on Amines: New Synthetic Adventures of Nitrogen Radical Cations. Synlett 2012, 1851-1856.
2. Ischay, M. A.; Yoon, T. P. Accessing the Synthetic Chemistry of Radical Ions. Eur. J. Org. Chem. 2012, 3359-3372.
3. Ravelli, D.; Fagnoni, M. Dyes as Visible Light Photoredox Organocatalysts. ChemCatChem 2012, 4, 169-171.
4. Oelgemöller, M.; Jung, C.; Mattay, J. Green Photochemistry: Production of Fine Chemicals with Sunlight. Pure Appl. Chem.2007, 79, 1939-1947.
5. Hoffmann, N. Homogeneous Photocatalytic Reactions with Organometallic and Coordination Compounds-Perspectives for Sustainable Chemistry. ChemSusChem 2012, 5, 352-371.
6. Vesely, J.; Rios, R. Organocatalytic Enantioselective α-Alkylation of Aldehydes. ChemCatChem 2012, 4, 942-953.
7. Lykakis, I. N.; Evgenidou, E.; Orfanopoulos, M. Photo-catalysis and Polyoxo-anion Decatungstate in Organic Chemistry: A Manifold Concept for Green Chemistry. Curr. Org. Chem. 2012, 16, 2400-2414.
8. Hoffmann, N. Photochemical Reactions as Key Steps in Organic Synthesis. Chem. Rev. 2008, 108, 1052-1103.
9. Protti, S.; Dondi, D.; Fagnoni, M.; Albini, A. Photochemistry in Synthesis: Where, When, and Why. Pure Appl. Chem. 2007, 79, 1929-1938.
10. Ravelli, D.; Fagnoni, M.; Albini, A. Photoorganocatalysis. What For? Chem. Soc. Rev. 2012, 42, 97.
11. Shi, L.; Xia, W. Photoredox Functionalization of C-H Bonds Adjacent to a Nitrogen Atom. Chem. Soc. Rev. 2012, 41, 7687.
12. Wallentin, C.-J.; Nguyen, J. D.; Stephenson, C. R. J. Radical Carbon-Carbon Bond Formations Enabled by Visible Light Active Photocatalysts. Chimia 2012, 66, 394-398.
13. Oelgemöller, M.; Shvydkiv, O. Recent Advances in Microflow Photochemistry. Molecules 2011, 16, 7522-7550.
14. Tucker, J. W.; Stephenson, C. R. J. Shining Light on Photoredox Catalysis: Theory and Synthetic Applications. J. Org. Chem. 2012, 77, 1617-1622.
15. Xi, Y.; Yi, H.; Lei, A. Synthetic Applications of Photoredox Catalysis with Visible Light. Org. Biomol. Chem. 2013, 11, 2387.
16. Roy, S. C.; Varghese, O. K.; Paulose, M.; Grimes, C. A. Toward Solar Fuels: Photocatalytic Conversion of Carbon Dioxide to Hydrocarbons. Acs Nano 2010, 4, 1259-1278.
17. Zhao, J.; Wu, W.; Sun, J.; Guo, S. Triplet Photosensitizers: From Molecular Design to Applications. Chem. Soc. Rev. 2013, 42, 5323.
18. Narayanam, J. M.; Stephenson, C. R. Visible Light Photoredox Catalysis: Applications in Organic Synthesis. Chem. Soc. Rev. 2011, 40, 102-113.
19. Xuan, J.; Xiao, W.-J. Visible-Light Photoredox Catalysis. Angew. Chem. Int. Ed. 2012, 51, 6828-6838.
20. Fagnoni, M.; Dondi, D.; Ravelli, D.; Albini, A. Photocatalysis for the Formation of the C-C Bond. Chem. Rev. 2007, 107, 2725-2756.
21. Ravelli, D.; Dondi, D.; Fagnoni, M.; Albini, A. Photocatalysis. A Multifaceted Concept for Green Chemistry. Chem. Soc. Rev.2009, 38, 1999.
22. Hoffmann, N. Efficient Photochemical Electron Transfer Sensitization of Homogeneous Organic Reactions. J. Photochem. Photobiol. C Photochem. Rev.2008, 9, 43-60.
23. Parmon, V. Photocatalysis as a Phenomenon: Aspects of Terminology. Catal. Today 1997, 39, 137-144.
24. Xi, W.; Krieger, M.; Kloxin, C. J.; Bowman, C. N. A New Photoclick Reaction Strategy: Photo-induced Catalysis of the thiol-Michael Addition via a Caged Primary Amine. Chem. Commun. 2013, 49, 4504.
25. Neilson, B. M.; Bielawski, C. W. Photoswitchable Organocatalysis: Using Light To Modulate the Catalytic Activities of N-Heterocyclic Carbenes. J. Am. Chem. Soc.2012, 134, 12693-12699.
26. Shvydkiv, O.; Yavorskyy, A.; Tan, S. B.; Nolan, K.; Hoffmann, N.; Youssef, A.; Oelgemöller, M. Microphotochemistry: a Reactor Comparison Study Using the Photosensitized Addition of Isopropanol to Furanones as a Model Reaction. Photochem. Photobiol. Sci. 2011, 10, 1399.
27. Corro, G.; Pal, U.; Tellez, N. Biodiesel Production from Jatropha Curcas Crude Oil Using ZnO/SiO2 Photocatalyst for Free Fatty Acids Esterification. Appl. Catal. B Environ. 2013, 129, 39-47.
28. Hall, J. F. B.; Bourne, R. A.; Han, X.; Earley, J. H.; Poliakoff, M.; George, M. W. Synthesis of Antimalarial Trioxanes via Continuous Photo-oxidation with 1O2 in Supercritical CO2. Green Chem. 2013, 15, 177.
29. Andrews, R. S.; Becker, J. J.; Gagné, M. R. A Photoflow Reactor for the Continuous Photoredox-Mediated Synthesis ofC-Glycoamino Acids andCGlycolipids. Angew. Chem. Int. Ed. 2012, 51, 4140-4143.
30. Neumann, M.; Zeitler, K. Application of Microflow Conditions to Visible Light Photoredox Catalysis. Org. Lett. 2012, 14, 2658-2661.
31. Nguyen, J. D.; Reiß, B.; Dai, C.; Stephenson, C. R. J. Batch to Flow Deoxygenation Using Visible Light Photoredox Catalysis. Chem. Commun.2013, 49, 4352.
32. Shvydkiv, O.; Nolan, K.; Oelgemöller, M. Microphotochemistry: 4,4’-Dimethoxybenzophenone Mediated Photodecarboxylation Reactions Involving Phthalimides. Beilstein J. Org. Chem. 2011, 7, 1055-1063.
33. Shvydkiv, O.; Yavorskyy, A.; Nolan, K.; Youssef, A.; Riguet, E.; Hoffmann, N.; Oelgemöller, M. Photosensitized Addition of Isopropanol to Furanones in a 365 Nm UV-LED Microchip. Photochem. Photobiol. Sci. 2010, 9, 1601.
34. Tucker, J. W.; Zhang, Y.; Jamison, T. F.; Stephenson, C. R. J. Visible-Light Photoredox Catalysis in Flow. Angew. Chem. Int. Ed. 2012, 51, 4144-4147.
35. Wang, H.; Partch, R. E.; Li, Y. Synthesis of 2-Alkylbenzimidazoles via TiO2-Mediated Photocatalysis. J. Org. Chem. 1997, 62, 5222-5225.
36. Sahoo, B.; Hopkinson, M. N.; Glorius, F. Combining Gold and Photoredox Catalysis: Visible Light-Mediated Oxy-and Aminoarylation of Alkenes. J. Am. Chem. Soc. 2013, 135, 5505-5508.
37. Manley, D. W.; McBurney, R. T.; Miller, P.; Howe, R. F.; Rhydderch, S.; Walton, J. C. Unconventional Titania Photocatalysis: Direct Deployment of Carboxylic Acids in Alkylations and Annulations. J. Am. Chem. Soc. 2012, 134, 13580-13583.
38. Montanaro, S.; Ravelli, D.; Merli, D.; Fagnoni, M.; Albini, A. Decatungstate As Photoredox Catalyst: Benzylation of Electron-Poor Olefins. Org. Lett. 2012, 14, 4218-4221.
39. Reinheimer, A.; Eldik, R. van; Kisch, H. On the Mechanism of Radical C-N Coupling in Type B Semiconductor Photocatalysis: A High-Pressure Study † , §. J. Phys. Chem. B 2000, 104, 1014-1024.
40. Miyake, Y.; Nakajima, K.; Nishibayashi, Y. Direct sp3C-H Amination of Nitrogen-Containing Benzoheterocycles Mediated by Visible-Light-Photoredox Catalysts. Chem. -Eur. J.2012, 18, 16473-16477.
41. Yoon, H.-S.; Ho, X.-H.; Jang, J.; Lee, H.-J.; Kim, S.-J.; Jang, H.-Y. N719 Dye-Sensitized Organophotocatalysis: Enantioselective Tandem Michael Addition/Oxyamination of Aldehydes. Org. Lett. 2012, 14, 3272-3275.
42. Espelt, L. R.; Wiensch, E. M.; Yoon, T. P. Brønsted Acid Cocatalysts in Photocatalytic Radical Addition of α-Amino C-H Bonds Across Michael Acceptors. J. Org. Chem.2013, 78, 4107-4114.
43. Kohls, P.; Jadhav, D.; Pandey, G.; Reiser, O. Visible Light Photoredox Catalysis: Generation and Addition ofN-Aryltetrahydroisoquinoline-Derived α-Amino Radicals to Michael Acceptors. Org. Lett. 2012, 14, 672-675.
44. Zhu, S.; Das, A.; Bui, L.; Zhou, H.; Curran, D. P.; Rueping, M. Oxygen Switch in Visible-Light Photoredox Catalysis: Radical Additions and Cyclizations and Unexpected C-C-Bond Cleavage Reactions. J. Am. Chem. Soc. 2013, 135, 1823-1829.
45. Miyake, Y.; Nakajima, K.; Nishibayashi, Y. Visible-Light-Mediated Utilization of α-Aminoalkyl Radicals: Addition to Electron-Deficient Alkenes Using Photoredox Catalysts. J. Am. Chem. Soc. 2012, 134, 3338-3341.
46. Andrews, R. S.; Becker, J. J.; Gagné, M. R. Intermolecular Addition of Glycosyl Halides to Alkenes Mediated by Visible Light. Angew. Chem. Int. Ed. 2010, 49, 7274-7276.
47. Courant, T.; Masson, G. Photoredox-Initiated alpha-Alkylation of Imines through a Three-Component Radical/Cationic Reaction. Chem.-Eur. J. 2012, 18, 423-427.
48. Wallentin, C.-J.; Nguyen, J. D.; Finkbeiner, P.; Stephenson, C. R. J. Visible Light-Mediated Atom Transfer Radical Addition via Oxidative and Reductive Quenching of Photocatalysts. J. Am. Chem. Soc. 2012, 134, 8875-8884.
49. Tyson, E. L.; Ament, M. S.; Yoon, T. P. Transition Metal Photoredox Catalysis of Radical Thiol-Ene Reactions. J. Org. Chem.2013, 78, 2046-2050.
50. Hopfner, M.; Weiβ, H.; Meissner, D.; Heinemann, F. W.; Kisch, H. Semiconductor Photocatalysis Type B: Synthesis of Unsaturated α-amino Esters from Imines and Olefins Photocatalyzed by Silica-supported Cadmium sulfide. Photochem. Photobiol. Sci. 2002, 1, 696-703.
51. Schindler, W.; Kisch, H. Heterogeneous Photocatalysis XV. Mechanistic Aspects of Cadmium Sulfide-catalyzed Photoaddition of Olefins to Schiff Bases. J. Photochem. Photobiol. Chem. 1997, 103, 257-264.
52. Pirtsch, M.; Paria, S.; Matsuno, T.; Isobe, H.; Reiser, O. Cu(dap)2Cl. As An Efficient Visible-Light-Driven Photoredox Catalyst in Carbon-Carbon Bond-Forming Reactions. Chem. -Eur. J. 2012, 18, 7336-7340.
53. Yoshida, H.; Fujimura, Y.; Yuzawa, H.; Kumagai, J.; Yoshida, T. A Heterogeneous Palladium Catalyst Hybridised with a Titanium Dioxide Photocatalyst for Direct C-C Bond Formation Between an Aromatic Ring and Acetonitrile. Chem. Commun.2013, 49, 3793.
54. Möhlmann, L.; Baar, M.; Rieß, J.; Antonietti, M.; Wang, X.; Blechert, S. Carbon Nitride-Catalyzed Photoredox C-C Bond Formation with NAryltetrahydroisoquinolines. Adv. Synth. Catal. 2012, 354, 1909-1913.
55. Rueping, M.; Zoller, J.; Fabry, D. C.; Poscharny, K.; Koenigs, R. M.; Weirich, T. E.; Mayer, J. Light-Mediated Heterogeneous Cross Dehydrogenative Coupling Reactions: Metal Oxides as Efficient, Recyclable, Photoredox Catalysts in C-C Bond-Forming Reactions. Chem. -Eur. J.2012, 18, 3478-3481.
56. Liu, Q.; Li, Y.-N.; Zhang, H.-H.; Chen, B.; Tung, C.-H.; Wu, L.-Z. Reactivity and Mechanistic Insight into Visible-Light-Induced Aerobic Cross-Dehydrogenative Coupling Reaction by Organophotocatalysts. Chem. -Eur. J.2012, 18, 620-627.
57. Mitkina, T.; Stanglmair, C.; Setzer, W.; Gruber, M.; Kisch, H.; König, B. Visible Light Mediated Homo-and Heterocoupling of Benzyl Alcohols and Benzyl Amines on Polycrystalline Cadmium Sulfide. Org. Biomol. Chem. 2012, 10, 3556.
58. Xue, Q.; Xie, J.; Jin, H.; Cheng, Y.; Zhu, C. Highly Efficient Visible-lightinduced Aerobic Oxidative C-C, C-P Coupling from C-H Bonds Catalyzed by a Gold(iii)-complex. Org. Biomol. Chem. 2013, 11, 1606.
59. Wang, S.; Nai, C. T.; Jiang, X.-F.; Pan, Y.; Tan, C.-H.; Nesladek, M.; Xu, Q.-H.; Loh, K. P. Graphene Oxide-Polythiophene Hybrid with Broad-Band Absorption and Photocatalytic Properties. J. Phys. Chem. Lett. 2012, 3, 2332-2336.
60. Cherevatskaya, M.; Neumann, M.; Füldner, S.; Harlander, C.; Kümmel, S.; Dankesreiter, S.; Pfitzner, A.; Zeitler, K.; König, B. Visible-Light-Promoted Stereoselective Alkylation by Combining Heterogeneous Photocatalysis with Organocatalysis. Angew. Chem. Int. Ed. 2012, 51, 4062-4066.
61. DiRocco, D. A.; Rovis, T. Catalytic Asymmetric alpha-Acylation of Tertiary Amines Mediated by a Dual Catalysis Mode: N-Heterocyclic Carbene and Photoredox Catalysis. J. Am. Chem. Soc. 2012, 134, 8094-8097.
62. Rueping, M.; Koenigs, R. M.; Poscharny, K.; Fabry, D. C.; Leonori, D.; Vila, C. Dual Catalysis: Combination of Photocatalytic Aerobic Oxidation and Metal Catalyzed Alkynylation Reactions-C-C Bond Formation Using Visible Light. Chem. -Eur. J.2012, 18, 5170-5174.
63. Wu, P.; He, C.; Wang, J.; Peng, X.; Li, X.; An, Y.; Duan, C. Photoactive Chiral Metal-Organic Frameworks for Light-Driven Asymmetric α-Alkylation of Aldehydes. J. Am. Chem. Soc.2012, 134, 14991-14999.
64. Jiang, H.; Huang, C.; Guo, J.; Zeng, C.; Zhang, Y.; Yu, S. Direct C-H Functionalization of Enamides and Enecarbamates by Using Visible-Light Photoredox Catalysis. Chem.-Eur. J. 2012, 18, 15158-15166.
65. Iqbal, N.; Choi, S.; Kim, E.; Cho, E. J. Trifluoromethylation of Alkenes by Visible Light Photoredox Catalysis. J. Org. Chem.2012, 77, 11383-11387.
66. Iqbal, N.; Choi, S.; Ko, E.; Cho, E. J. Trifluoromethylation of Heterocycles via Visible Light Photoredox Catalysis. Tetrahedron Lett.2012, 53, 2005-2008.
67. Ye, Y.; Sanford, M. S. Merging Visible-Light Photocatalysis and Transition-Metal Catalysis in the Copper-Catalyzed Trifluoromethylation of Boronic Acids with CF3I. J. Am. Chem. Soc. 2012, 134, 9034-9037.
68. Mizuta, S.; Engle, K. M.; Verhoog, S.; Galicia-López, O.; O’Duill, M.; Médebielle, M.; Wheelhouse, K.; Rassias, G.; Thompson, A. L.; Gouverneur, V. Trifluoromethylation of Allylsilanes Under Photoredox Catalysis. Org. Lett. 2013, 15, 1250-1253.
69. Yasu, Y.; Koike, T.; Akita, M. Visible-light-induced Synthesis of a Variety of Trifluoromethylated Alkenes from Potassium Vinyltrifluoroborates by Photoredox Catalysis. Chem. Commun.2013, 49, 2037.
70. Wang, Z.-Q.; Hu, M.; Huang, X.-C.; Gong, L.-B.; Xie, Y.-X.; Li, J.-H. Direct α-Arylation of α-Amino Carbonyl Compounds with Indoles Using Visible Light Photoredox Catalysis. J. Org. Chem.2012, 77, 8705-8711.
71. Zhu, S.; Rueping, M. Merging Visible-light Photoredox and Lewis Acid Catalysis for the Functionalization and Arylation of Glycine Derivatives and Peptides. Chem. Commun. 2012, 48, 11960.
72. Yoo, W.-J.; Tanoue, A.; Kobayashi, S. Aerobic Oxidation of a Tertiary Aliphatic Amine Under Visible-Light Photocatalysis: Facile Synthesis of Methylene-Bridged Bis-1,3-dicarbonyl Compounds. Chem. -Asian J. 2012, 7, 2764-2767.
73. Nicewicz, D. A.; MacMillan, D. W. C. Merging Photoredox Catalysis with Organocatalysis: The Direct Asymmetric Alkylation of Aldehydes. Science 2008, 322, 77-80.
74. Tao, Y.-T.; Yeh, W.-L.; Tu, C.-L.; Chow, Y. L. Acidity Effects on Lightpromoted Carbonylation of Olefins in the Presence of Cobalt Catalysis. J. Mol. Catal. 1991, 67, 105-115.
75. Goes, A. D. S.; Ferroud, C.; Santamaria, J. Regioselective Single Electron Transfer Photocatalytic Synthesis of 2-cyano-3-ethylidenepiperidines. New Route to the Total Synthesis of (±) Cis-eburnamonine. Tetrahedron Lett.1995, 36, 2235-2238.
76. To, W.-P.; Liu, Y.; Lau, T.-C.; Che, C.-M. A Robust Palladium(II)-Porphyrin Complex as Catalyst for Visible Light Induced Oxidative C-H Functionalization. Chem.-Eur. J. 2013, 19, 5654-5664.
77. To, W.-P.; Tong, G. S.-M.; Lu, W.; Ma, C.; Liu, J.; Chow, A. L.-F.; Che, C.-M. Luminescent Organogold(III) Complexes with Long-Lived Triplet Excited States for Light-Induced Oxidative C-H Bond Functionalization and Hydrogen Production. Angew. Chem.-Int. Ed. 2012, 51, 2654-2657.
78. Hoshikawa, T.; Yoshioka, S.; Kamijo, S.; Inoue, M. Photoinduced Direct Cyanation of C(sp(3))-H Bonds. Synth.-Stuttg.2013, 45, 874-887.
79. Ferroud, C.; Cocquet, G.; Guy, A. Photooxidations of 1,1-dialkyl-2-arylhydrazines by Single Electron Transfer. Tetrahedron Lett. 1999, 40, 5005-5008.
80. Jiang, H.; Chen, X.; Zhang, Y.; Yu, S. C-H Functionalization of Enamides: Synthesis of β-Amidovinyl SulfonesviaVisible-Light Photoredox Catalysis. Adv. Synth. Catal. 2013, 355, 809-813.
81. Rao, H.; Wang, P.; Li, C.-J. Visible-Light-Triggered Direct Benzoyloxy-lation of Electron-Rich Arenes at Room Temperature Without Chelation Assistance. Eur. J. Org. Chem. 2012, 6503-6507.
82. Zhao, J.; Zheng, Z.; Bottle, S.; Chou, A.; Sarina, S.; Zhu, H. Highly Efficient and Selective Photocatalytic Hydroamination of Alkynes by Supported Gold Nanoparticles Using Visible Light at Ambient Temperature. Chem. Commun.2013, 49, 2676.
83. Shiraishi, Y.; Fujiwara, K.; Sugano, Y.; Ichikawa, S.; Hirai, T. NMonoalkylation of Amines with Alcohols by Tandem Photocatalytic and Catalytic Reactions on TiO2Loaded with Pd Nanoparticles. Acs Catal. 2013, 3, 312-320.
84. Teo, Y. C.; Pan, Y.; Tan, C. H. Organic Dye-Photocatalyzed Acylnitroso Ene Reaction. ChemCatChem 2013, 5, 235-240.
85. Rueping, M.; Vila, C.; Szadkowska, A.; Koenigs, R. M.; Fronert, J. Photoredox Catalysis as an Efficient Tool for the Aerobic Oxidation of Amines and Alcohols: Bioinspired Demethylations and Condensations. Acs Catal. 2012, 2, 2810-2815.
86. Rao, K. V. S.; Subrahmanyam, M. Synthesis of 2-methylpiperazine by Photocatalytic Reaction in a Non-aqueous Suspension of Semiconductor-Zeolite Composite Catalysts. Photochem. Photobiol. Sci. 2002, 1, 597-599.
87. Rao, K. V. S.; Srinivas, B.; Subrahmanyam, M.; Prasad, A. R. A Novel One Step Photocatalytic Synthesis of Dihydropyrazine from Ethylenediamine and Propylene Glycol. Chem. Commun. 2000, 1533-1534.
88. Maity, S.; Zheng, N. A Visible-Light-Mediated Oxidative C-N Bond Formation/ Aromatization Cascade: Photocatalytic Preparation of N-Arylindoles. Angew. Chem. Int. Ed. 2012, 51, 9562-9566.
89. Cheng, Y.; Yang, J.; Qu, Y.; Li, P. Aerobic Visible-Light Photoredox Radical C-H Functionalization: Catalytic Synthesis of 2-Substituted Benzothiazoles. Org. Lett. 2012, 14, 98-101.
90. Hakki, A.; Dillert, R.; Bahnemann, D. W. Factors Affecting the Selectivity of the Photocatalytic Conversion of Nitroaromatic Compounds over TiO2 to Valuable Nitrogen-containing Organic Compounds. Phys. Chem. Chem. Phys. 2013, 15, 2992.
91. Hakki, A.; Dillert, R.; Bahnemann, D. W. Arenesulfonic Acid-Functionalized Mesoporous Silica Decorated with Titania: A Heterogeneous Catalyst for the One-Pot Photocatalytic Synthesis of Quinolines from Nitroaromatic Compounds and Alcohols. Acs Catal. 2013, 3, 565-572.
92. Park, K. H.; Joo, H. S.; Ahn, K. I.; Jun, K. One Step Synthesis of 4-ethoxy-1,2,3,4-tetrahydroquinoline from Nitroarene and Ethanol: A TiO2 Mediated Photocatalytic Reaction. Tetrahedron Lett. 1995, 36, 5943-5946.
93. Xia, J.-D.; Deng, G.-B.; Zhou, M.-B.; Liu, W.; Xie, P.; Li, J.-H. Reusable Visible Light Photoredox Catalysts; Catalyzed Benzylic C(sp(3))-H Functionalization/ Carbocyclization Reactions. Synlett 2012, 2707-2713.
94. Xuan, J.; Feng, Z.-J.; Duan, S.-W.; Xiao, W.-J. Room Temperature Synthesis of Isoquino[2,1-a][3,1]oxazine and Isoquino [2,1-a]pyrimidine Derivatives via Visible Light Photoredox Catalysis. Rsc Adv. 2012, 2, 4065.
95. Mathis, C. L.; Gist, B. M.; Frederickson, C. K.; Midkiff, K. M.; Marvin, C. C. Visible Light Photooxidative Cyclization of Amino Alcohols to 1,3-oxazines. Tetrahedron Lett. 2013, 54, 2101-2104.
96. Ananthakrishnan, R.; Gazi, S. [Ru(bpy)3]2+ Aided Photocatalytic Synthesis of 2-arylpyridines via Hantzsch Reaction Under Visible Irradiation and Oxygen Atmosphere. Catal. Sci. Technol. 2012, 2, 1463.
97. Ju, X.; Liang, Y.; Jia, P.; Li, W.; Yu, W. Synthesis of Oxindoles via Visible Light Photoredox Catalysis. Org. Biomol. Chem. 2011, 10, 498.
98. Hernandez-Perez, A. C.; Vlassova, A.; Collins, S. K. Toward a Visible Light Mediated Photocyclization: Cu-Based Sensitizers for the Synthesis of [5] Helicene. Org. Lett. 2012, 14, 2988-2991.
99. Hari, D. P.; Hering, T.; König, B. Visible Light Photocatalytic Synthesis of Benzothiophenes. Org. Lett. 2012, 14, 5334-5337.
100. Kim, H.; Lee, C. Visible-Light-Induced Photocatalytic Reductive Transformations of Organohalides. Angew. Chem. Int. Ed. 2012, 51, 12303-12306.
101. Lin, S.; Ischay, M. A.; Fry, C. G.; Yoon, T. P. Radical Cation Diels-Alder Cycloadditions by Visible Light Photocatalysis. J. Am. Chem. Soc.2011, 133, 19350-19353.
102. Sakata, T.; Kawai, T.; Hashimoto, K. Heterogeneous Photocatalytic Reactions of Organic Acids and Water. New Reaction Paths Besides the photo-Kolbe Reaction. J. Phys. Chem. 1984, 88, 2344-2350.
103. Moon, S.-C.; Fujino, M.; Yamashita, H.; Anpo, M. Characterization of Zirconium-Silicon Binary Oxide Catalysts Prepared by the Sol-Gel Method and Their Photocatalytic Activity for the Isomerization of 2-Butene. J. Phys. Chem. B 1997, 101, 369-373.
104. Zhang, S. G.; Higashimoto, S.; Yamashita, H.; Anpo, M. Characterization of Vanadium Oxide/ZSM-5 Zeolite Catalysts Prepared by the Solid-State Reaction and Their Photocatalytic Reactivity: In Situ Photoluminescence, XAFS, ESR, FT-IR, and UV-vis Investigations. J. Phys. Chem. B 1998, 102, 5590-5594.
105. Gao, G.; Deng, Y.; Kispert, L. D. Semiconductor Photocatalysis: Photodegradation and Trans-Cis Photoisomerization of Carotenoids. J. Phys. Chem. B 1998, 102, 3897-3901.
106. López-Tenllado, F. J.; Marinas, A.; Urbano, F. J.; Colmenares, J. C.; Hidalgo, M. C.; Marinas, J. M.; Moreno, J. M. Selective Photooxidation of Alcohols as Test Reaction for Photocatalytic Activity. Appl. Catal. B Environ. 2012, 128, 150-158.
107. Pillai, U. R.; Sahle-Demessie, E. Selective Oxidation of Alcohols in Gas Phase Using Light-Activated Titanium Dioxide. J. Catal. 2002, 211, 434-444.
108. Zhang, N.; Zhang, Y.; Yang, M.-Q.; Tang, Z.-R.; Xu, Y.-J. A Critical and Benchmark Comparison on Graphene-, Carbon Nanotube-, and Fullerenesemiconductor Nanocomposites as Visible Light Photocatalysts for Selective Oxidation. J. Catal. 2013, 299, 210-221.
109. Zou, Y.-Q.; Chen, J.-R.; Liu, X.-P.; Lu, L.-Q.; Davis, R. L.; Jørgensen, K. A.; Xiao, W.-J. Highly Efficient Aerobic Oxidative Hydroxylation of Arylboronic Acids: Photoredox Catalysis Using Visible Light. Angew. Chem. Int. Ed. 2012, 51, 784-788.
110. Hajimohammadi, M.; Schwarzinger, C.; Knör, G. Controlled Multistep Oxidation of Alcohols and Aldehydes to Carboxylic Acids Using Air, Sunlight and a Robust Metalloporphyrin Sensitizer with a pH-switchable Photoreactivity. Rsc Adv. 2012, 2, 3257.
111. Zhang, M.; Chen, C.; Ma, W.; Zhao, J. Visible-Light-Induced Aerobic Oxidation of Alcohols in a Coupled Photocatalytic System of Dye-Sensitized TiO2and TEMPO. Angew. Chem.2008, 120, 9876-9879.
112. Naya, S.; Kimura, K.; Tada, H. One-Step Selective Aerobic Oxidation of Amines to Imines by Gold Nanoparticle-Loaded Rutile Titanium(IV) Oxide Plasmon Photocatalyst. Acs Catal. 2013, 3, 10-13.
113. Tang, Z.-R.; Zhang, Y.; Xu, Y.-J. Tuning the Optical Property and Photocatalytic Performance of Titanate Nanotube Toward Selective Oxidation of Alcohols Under Ambient Conditions. Acs Appl. Mater. Interfaces 2012, 4, 1512-1520.
114. Imamura, K.; Tsukahara, H.; Hamamichi, K.; Seto, N.; Hashimoto, K.; Kominami, H. Simultaneous Production of Aromatic Aldehydes and Dihydrogen by Photocatalytic Dehydrogenation of Liquid Alcohols over Metalloaded titanium(IV) Oxide Under Oxidant-and Solvent-free Conditions. Appl. Catal. Gen.2013, 450, 28-33.
115. Zhang, N.; Zhang, Y.; Pan, X.; Yang, M.-Q.; Xu, Y.-J. Constructing Ternary CdS-Graphene-TiO2Hybrids on the Flatland of Graphene Oxide with Enhanced Visible-Light Photoactivity for Selective Transformation. J. Phys. Chem. C 2012, 116, 18023-18031.
116. Hattori, H.; Ide, Y.; Ogo, S.; Inumaru, K.; Sadakane, M.; Sano, T. Efficient and Selective Photocatalytic Cyclohexane Oxidation on a Layered Titanate Modified with Iron Oxide Under Sunlight and CO2Atmosphere. Acs Catal. 2012, 2, 1910-1915.
117. Rueping, M.; Vila, C.; Szadkowska, A.; Koenigs, R. M.; Fronert, J. Photoredox Catalysis as an Efficient Tool for the Aerobic Oxidation of Amines and Alcohols: Bioinspired Demethylations and Condensations. Acs Catal. 2012, 2, 2810-2815.
118. Maeda, Y.; Niino, Y.; Kondo, T.; Yamada, M.; Hasegawa, T.; Akasaka, T. Oxygen Atom Transfer from Peroxide Intermediates to Fullerenes. Chem. Lett. 2011, 40, 1431-1433.
119. Noceti, R. P.; Taylor, C. E.; D’Este, J. R. Photocatalytic Conversion of Methane. Catal. Today 1997, 33, 199-204.
120. Zou, Y.-Q.; Chen, J.-R.; Liu, X.-P.; Lu, L.-Q.; Davis, R. L.; Jørgensen, K. A.; Xiao, W.-J. Highly Efficient Aerobic Oxidative Hydroxylation of Arylboronic Acids: Photoredox Catalysis Using Visible Light. Angew. Chem. Int. Ed. 2012, 51, 784-788.
121. Panagiotou, G. D.; Tzirakis, M. D.; Vakros, J.; Loukatzikou, L.; Orfanopoulos, M.; Kordulis, C.; Lycourghiotis, A. Development of [60] Fullerene Supported on Silica Catalysts for the Photo-oxidation of Alkenes. Appl. Catal. Gen. 2010, 372, 16-25.
122. Fukuoka, A.; Fujishima, K.; Chiba, M.; Yamagishi, A.; Inagaki, S.; Fukushima, Y.; Ichikawa, M. Photooxidation of Cyclohexene and Benzene with Oxygen by Fullerenes Grafted on Mesoporous FSM-16. Catal. Lett. 2000, 68, 241-244.
123. Tagmatarchis, N.; Shinohara, H.; Fujitsuka, M.; Ito, O. Photooxidation of Olefins Sensitized by Bisazafullerene (C 59 N) 2 and Hydroazafullerene C 59 HN: Product Analysis, Emission of Singlet Oxygen, and Transient Absorption Spectroscopy. J. Org. Chem.2001, 66, 8026-8029.
124. Takaguchi, Y.; Yanagimoto, Y.; Fujima, S.; Tsuboi, S. Photooxygenation of Olefins, Phenol, and Sulfide Using Fullerodendrimer as Catalyst. Chem. Lett. 2004, 33, 1142-1143.
125. Tzirakis, M. D.; Vakros, J.; Loukatzikou, L.; Amargianitakis, V.; Orfanopoulos, M.; Kordulis, C.; Lycourghiotis, A. gamma-Alumina-supported [60]fullerene Catalysts: Synthesis, Properties and Applications in the Photooxidation of Alkenes. J. Mol. Catal. -Chem. 2010, 316, 65-74.
126. Kyriakopoulos, J.; Tzirakis, M. D.; Panagiotou, G. D.; Alberti, M. N.; Triantafyllidis, K. S.; Giannakaki, S.; Bourikas, K.; Kordulis, C.; Orfanopoulos, M.; Lycourghiotis, A. Highly Active Catalysts for the Photooxidation of Organic Compounds by Deposition of [60] Fullerene onto the MCM-41 Surface: A Green Approach for the Synthesis of Fine Chemicals. Appl. Catal. B Environ. 2012, 117-118, 36-48.
127. Nguyen, V.-H.; Wu, J. C. S.; Bai, H. Temperature Effect on the Photoepoxidation of Propylene over V-Ti/MCM-41 Photocatalyst. Catal. Commun. 2013, 33, 57-60.
128. O’Shea, K. E.; Jannach, S. H.; Garcia, I. The Reactions of Substituted Acyclic 1,3-butadienes on Photoexcited TiO2 in Acetonitrile. J. Photochem. Photobiol. Chem. 1999, 122, 127-131.
129. Kuriacose, J. Conversion of Isopropyl Alcohol to Acetone on Irradiated Zinc Oxide*1. J. Catal. 1962, 1, 498-507.
130. Murcia, J. J.; Hidalgo, M. C.; Navío, J. A.; Vaiano, V.; Ciambelli, P.; Sannino, D. Ethanol Partial Photoxidation on Pt/TiO2 Catalysts as Green Route for Acetaldehyde Synthesis. Catal. Today 2012, 196, 101-109.
131. Yang, M.-Q.; Zhang, N.; Xu, Y.-J. Synthesis of Fullerene-, Carbon Nanotube-, and Graphene-TiO 2 Nanocomposite Photocatalysts for Selective Oxidation: A Comparative Study. Acs Appl. Mater. Interfaces 2013, 5, 1156-1164.
132. Nasalevich, M. A.; Kozlova, E. A.; Lyubina, T. P.; Vorontsov, A. V. Photocatalytic Oxidation of Ethanol and Isopropanol Vapors on Cadmium Sulfide. J. Catal. 2012, 287, 138-148.
133. Liu, S.; Zhang, N.; Tang, Z.-R.; Xu, Y.-J. Synthesis of One-Dimensional CdS@TiO2Core-Shell Nanocomposites Photocatalyst for Selective Redox: The Dual Role of TiO2Shell. Acs Appl. Mater. Interfaces 2012, 4, 6378-6385.
134. Long, J.; Wang, S.; Ding, Z.; Wang, S.; Zhou, Y.; Huang, L.; Wang, X. Amine-functionalized Zirconium Metal-organic Framework as Efficient Visible-light Photocatalyst for Aerobic Organic Transformations. Chem. Commun.2012, 48, 11656.
135. Zhang, M.; Chen, C.; Ma, W.; Zhao, J. Visible-Light-Induced Aerobic Oxidation of Alcohols in a Coupled Photocatalytic System of Dye-Sensitized TiO2and TEMPO. Angew. Chem.2008, 120, 9876-9879.
136. Özcan, L.; Yurdakal, S.; Augugliaro, V.; Loddo, V.; Palmas, S.; Palmisano, G.; Palmisano, L. Photoelectrocatalytic Selective Oxidation of 4-methoxybenzyl Alcohol in Water by TiO2 Supported on Titanium Anodes. Appl. Catal. B Environ. 2013, 132-133, 535-542.
137. Dadová, J.; Kümmel, S.; Feldmeier, C.; Cibulková, J.; Pažout, R.; Maixner, J.; Gschwind, R. M.; König, B.; Cibulka, R. Aggregation Effects in Visible-Light Flavin Photocatalysts: Synthesis, Structure, and Catalytic Activity of 10-Arylflavins. Chem. -Eur. J. 2013, 19, 1066-1075.
138. Zhang, Y.; Zhang, N.; Tang, Z.-R.; Xu, Y.-J. Graphene Transforms Wide Band Gap ZnS to a Visible Light Photocatalyst. The New Role of Graphene as a Macromolecular Photosensitizer. Acs Nano 2012, 6, 9777-9789.
139. Parrish, J. D.; Ischay, M. A.; Lu, Z.; Guo, S.; Peters, N. R.; Yoon, T. P. Endoperoxide Synthesis by Photocatalytic Aerobic [2 + 2 + 2] Cycloadditions. Org. Lett. 2012, 14, 1640-1643.
140. Naya, S.; Kimura, K.; Tada, H. One-Step Selective Aerobic Oxidation of Amines to Imines by Gold Nanoparticle-Loaded Rutile Titanium(IV) Oxide Plasmon Photocatalyst. Acs Catal. 2013, 3, 10-13.
141. Wu, W.; Wen, L.; Shen, L.; Liang, R.; Yuan, R.; Wu, L. A New Insight into the Photocatalytic Reduction of 4-nitroaniline to P-phenylenediamine in the Presence of Alcohols. Appl. Catal. B Environ. 2013, 130-131, 163-167.
142. Shiraishi, Y.; Togawa, Y.; Tsukamoto, D.; Tanaka, S.; Hirai, T. Highly Efficient and Selective Hydrogenation of Nitroaromatics on Photoactivated Rutile Titanium Dioxide. Acs Catal. 2012, 2, 2475-2481.
143. Kamegawa, T.; Seto, H.; Matsuura, S.; Yamashita, H. Preparation of Hydroxynaphthalene-Modified TiO2 via Formation of Surface Complexes and Their Applications in the Photocatalytic Reduction of Nitrobenzene Under Visible-Light Irradiation. Acs Appl. Mater. Interfaces 2012, 4, 6635-6639.
144. Ferry, J. L.; Glaze, W. H. Photocatalytic Reduction of Nitro Organics over Illuminated Titanium Dioxide: Role of the TiO2Surface. Langmuir 1998, 14, 3551-3555.
145. Pal, B.; Torimoto, T.; Okazaki, K.; Ohtani, B. Photocatalytic Syntheses of Azoxybenzene by Visible Light Irradiation of Silica-coated Cadmium Sulfide Nanocomposites. Chem. Commun.2007, 483.
146. Kohtani, S.; Yoshioka, E.; Saito, K.; Kudo, A.; Miyabe, H. Adsorptive and Kinetic Properties on Photocatalytic Hydrogenation of Aromatic Ketones Upon UV Irradiated Polycrystalline Titanium Dioxide: Differences Between Acetophenone and Its Trifluoromethylated Derivative. J. Phys. Chem. C 2012, 116, 17705-17713.
147. Tada, H.; Teranishi, K.; Inubushi, Y.; Ito, S. Ag Nanocluster Loading Effect on TiO2 Photocatalytic Reduction of Bis(2-dipyridyl)disulfide to 2-Mercaptopyridine by H 2 O. Langmuir 2000, 16, 3304-3309.
148. Tada, H.; Teranishi, K.; Ito, S. Additive Effect of Sacrificial Electron Donors on Ag/TiO2Photocatalytic Reduction of Bis(2-dipyridyl)disulfide to 2-Mercaptopyridine in Aqueous Media. Langmuir 1999, 15, 7084-7087.
149. Tada, H.; Suzuki, F.; Yoneda, S.; Ito, S.; Kobayashi, H. The Effect of Nanometre-sized Au Particle Loading on TiO2 Photocatalysed Reduction of Bis(2-dipyridyl)disulfide to 2-mercaptopyridine by H2O. Phys. Chem. Chem. Phys. 2001, 3, 1376-1382.
150. Khan, M. M. T.; Rao, N. N. Photocatalytic Hydrogenation of Cyclohexene through H2O as a Source of H2 by Pt/CdS/RuO2 Semiconductor Particulate System Catalysed by KRu(H—EDTA)Cl]2H2O. J. Mol. Catal.1990, 58, 323-329.
151. Ke, X.; Zhang, X.; Zhao, J.; Sarina, S.; Barry, J.; Zhu, H. Selective Reductions Using Visible Light Photocatalysts of Supported Gold Nanoparticles. Green Chem. 2013, 15, 236.
152. Subrahmanyam, M.; Kaneco, S.; Alonso-Vante, N. A Screening for the Photo Reduction of Carbon Dioxide Supported on Metal Oxide Catalysts for C1-C3 Selectivity. Appl. Catal. B Environ. 1999, 23, 169-174.
153. Inoue, H.; Moriwaki, H.; Maeda, K.; Yoneyama, H. Photoreduction of Carbon Dioxide Using Chalcogenide Semiconductor Microcrystals. J. Photochem. Photobiol. Chem. 1995, 86, 191-196.
154. Yoneyama, H. Photoreduction of Carbon Dioxide on Quantized Semiconductor Nanoparticles in Solution. Catal. Today 1997, 39, 169-175.
155. Tseng, I.-H.; Wu, J. C. S.; Chou, H.-Y. Effects of Sol-gel Procedures on the Photocatalysis of Cu/TiO2 in CO2 Photoreduction. J. Catal. 2004, 221, 432-440.
156. Mizuno, T.; Adachi, K.; Ohta, K.; Saji, A. Effect of CO2 Pressure on Photocatalytic Reduction of CO2 Using TiO2 in Aqueous Solutions. J. Photochem. Photobiol. Chem. 1996, 98, 87-90.
157. Premkumar, J.; Ramaraj, R. Photocatalytic Reduction of Carbon Dioxide to Formic Acid at Porphyrin and Phthalocyanine Adsorbed Nafion Membranes. J. Photochem. Photobiol. Chem. 1997, 110, 53-58.
158. Johne, P.; Kisch, H. Photoreduction of Carbon Dioxide Catalysed by Free and Supported Zinc and Cadmium Sulphide Powders. J. Photochem. Photobiol. Chem. 1997, 111, 223-228.
159. Wang, Z.-Y.; Chou, H.-C.; Wu, J. C. S.; Tsai, D. P.; Mul, G. CO2 Photoreduction Using NiO/InTaO4 in Optical-fiber Reactor for Renewable Energy. Appl. Catal. Gen.2010, 380, 172-177.
160. Dunn, W. W.; Aikawa, Y.; Bard, A. J. Heterogeneous Photosynthetic Production of Amino Acids at Platinum/titanium Dioxide Suspensions by Near Ultraviolet Light. J. Am. Chem. Soc.1981, 103, 6893-6897.