Surface-Doped Graphitic Carbon Nitride Catalyzed Photooxidation of Olefins and Dienes: Chemical Evidence for Electron Transfer and Singlet Oxygen Mechanisms
Abstract
:1. Introduction
2. Results and Discussion
3. Materials and Methods
3.1. General
3.2. General Photooxidation Method
3.3. Synthesis of 2-(4-methoxyphenyl)-3-methylbut-2-ene (4)
3.4. Synthesis of 2-(1,1,1-trideuteromethyl)-5-methylhex-2-ene (2)
3.5. Synthesis of 1,1-di(p-anisyl)ethylene (5)
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
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Entry | Photocatalyst | Conversion (%) a | Irradiation Time (min) | Regioselectivities (%) b | ||
---|---|---|---|---|---|---|
2a | 2b | 2c | ||||
1 | TPP | 100 | 5 | 56 | 31 | 13 |
2 | CD-C3N4 | 34 | 30 | 58 | 29 | 13 |
Entry | Photocatalyst | Solvents | 4a % a | 4b % b | 4c % c | Conversion % |
---|---|---|---|---|---|---|
1 | TPP | CCl4 | 76 | 24 | - | 100d |
2 | RB | CDCl3 | 70 | 30 | - | 100d |
3 | MB | CH3CN | 66 | 34 | - | 100d |
4 | DCA | CD3CN | 61 | 27 | 12 | 87d |
5 | CD-C3N4 | CDCl3 | 53 | 31 | 16 | 80 |
6 | CD-C3N4 | CD3CN | 58 | 27 | 15 | 70 |
7 | CD-C3N4 | Benzene | 53 | 31 | 16 | 67 |
8 | CD-C3N4 | EtOAc | 53 | 29 | 18 | 65 |
9 | CD-C3N4 | EtOH | - | - | 100 | 100 |
10 | CD-C3N4 | CDCl3 | - | - | - | - e |
11 | no catalyst | CDCl3 | traces | traces | - | <1 f |
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Chatzoudis, A.; Giannopoulos, V.; Hollmann, F.; Smonou, I. Surface-Doped Graphitic Carbon Nitride Catalyzed Photooxidation of Olefins and Dienes: Chemical Evidence for Electron Transfer and Singlet Oxygen Mechanisms. Catalysts 2019, 9, 639. https://doi.org/10.3390/catal9080639
Chatzoudis A, Giannopoulos V, Hollmann F, Smonou I. Surface-Doped Graphitic Carbon Nitride Catalyzed Photooxidation of Olefins and Dienes: Chemical Evidence for Electron Transfer and Singlet Oxygen Mechanisms. Catalysts. 2019; 9(8):639. https://doi.org/10.3390/catal9080639
Chicago/Turabian StyleChatzoudis, Apostolos, Vasileios Giannopoulos, Frank Hollmann, and Ioulia Smonou. 2019. "Surface-Doped Graphitic Carbon Nitride Catalyzed Photooxidation of Olefins and Dienes: Chemical Evidence for Electron Transfer and Singlet Oxygen Mechanisms" Catalysts 9, no. 8: 639. https://doi.org/10.3390/catal9080639