Communication
Green Chemistry
2 M. Milan, M. Salamone, M. Costas and M. Bietti, Acc.
Chem. Res., 2018, 51, 1984–1995.
3 G. J. Ten Brink, I. Arends and R. A. Sheldon, Chem. Rev.,
2004, 104, 4105–4123.
4 A. A. Ghogare and A. Greer, Chem. Rev., 2016, 116, 9994–
10034.
5 Y. Nosaka and A. Y. Nosaka, Chem. Rev., 2017, 117, 11302–
11336.
6 T. Punniyamurthy, S. Velusamy and J. Iqbal, Chem. Rev.,
2005, 105, 2329–2363.
7 X. J. Lang, J. C. Zhao and X. D. Chen, Chem. Soc. Rev., 2016,
45, 3026–3038.
8 Z. Z. Shi, C. Zhang, C. H. Tang and N. Jiao, Chem. Soc. Rev.,
2012, 41, 3381–3430.
9 X. J. Lang, W. H. Ma, C. C. Chen, H. W. Ji and J. C. Zhao,
Acc. Chem. Res., 2014, 47, 355–363.
10 A. Savateev, I. Ghosh, B. Konig and M. Antonietti, Angew.
Chem., Int. Ed., 2018, 57, 15936–15947.
11 X. Z. Fan, J. W. Rong, H. L. Wu, Q. Zhou, H. P. Deng, J. Da
Tan, C. W. Xue, L. Z. Wu, H. R. Tao and J. Wu, Angew.
Chem., Int. Ed., 2018, 57, 8514–8518.
Scheme 2
. Comparison studies between the 1,6-PYD/IPA photo-
12 N. A. Romero and D. A. Nicewicz, Chem. Rev., 2016, 116,
10075–10166.
catalytic system and commercial 30% H2O2 aqueous solution.
13 D. Ravelli, M. Fagnoni and A. Albini, Chem. Soc. Rev., 2013,
42, 97–113.
14 W.-Z. Weng, H. Liang and B. Zhang, Org. Lett., 2018, 20,
4979–4983.
Conclusions
In conclusion, we discovered 1,6-PYD as an organophotocatalyst under
visible-light irradiation for oxygenation reactions. H2O2 was smoothly gen- 15 H. Wang, W. G. Li, K. Zeng, Y. J. Wu, Y. Zhang, T. L. Xu and
erated by 1,6-PYD in IPA in the presence of O2 under visible light, and
Y. Chen, Angew. Chem., Int. Ed., 2019, 58, 561–565.
this catalytic system can be applied to achieve effective epoxidation of elec- 16 K. Ohkubo, A. Fujimoto and S. Fukuzumi, Chem. Commun.,
tron-deficient alkenes, oxidative hydroxylation of organoborons, and selec-
2011, 47, 8515–8517.
tive oxidation of sulfides to sulfoxides. The results agreed well with those 17 X. Gu, X. Li, Y. Chai, Q. Yang, P. Li and Y. Yao, Green
obtained using commercial aqueous H2O2. This mild and metal-free pro-
Chem., 2013, 15, 357.
tocol, which uses oxygen as a terminal oxidant and IPA as a hydrogen 18 L. Cui, N. Tada, H. Okubo, T. Miura and A. Itoh, Green
donor and green solvent, is promising for its wide applications in oxi-
Chem., 2011, 13, 2347.
dative transformations, especially where the reaction components suffer 19 N. Tada, L. Cui, H. Okubo, T. Miura and A. Itoh, Adv. Synth.
from poor robustness in the presence of excess H2O2 or water.33
Catal., 2010, 352, 2383–2386.
20 L. Cui, S. Furuhashi, Y. Tachikawa, N. Tada, T. Miura and
A. Itoh, Tetrahedron Lett., 2013, 54, 162–165.
Conflicts of interest
21 K. Matsui, T. Ishigami, T. Yamaguchi, E. Yamaguchi,
N. Tada, T. Miura and A. Itoh, Synlett, 2014, 25, 2613–2616.
22 Y. Zhang, W. Yao, D. Liang, M. Sun, S. Wang and
D. Huang, Sens. Actuators, B., 2018, 259, 768–774.
23 M. Yasutake, T. Fujihara, A. Nagasawa, K. Moriya and
T. Hirose, Eur. J. Org. Chem., 2008, 2008, 4120–4125.
24 R. S. Becker and L. V. Natarajan, J. Phys. Chem., 1993, 97,
344–349.
25 X. Ji, C. E. Banks, D. S. Silvester, A. J. Wain and
R. G. Compton, J. Phys. Chem. C, 2007, 111, 1496–1504.
26 D. P. Valencia, P. D. Astudillo, A. Galano and F. J. González,
Org. Biomol. Chem., 2013, 11, 318–325.
The authors declare no competing financial interest.
Acknowledgements
The authors thank for the financial support provided by the
National University of Singapore and the Ministry of Education
(MOE) of Singapore (grant no: MOE2014-T2-1-134, MOE2017-
T2-2-081) and Natural Science Foundation of Jiangsu, China
(grant no: BK20141219).
27 M. Bancirova, Luminescence, 2011, 26, 685–688.
28 J. M. Campos-Martin, G. Blanco-Brieva and J. L. G. Fierro,
Angew. Chem., Int. Ed., 2006, 45, 6962–6984.
Notes and references
1 Y. F. Liang and N. Jiao, Acc. Chem. Res., 2017, 50, 1640– 29 T. Nishimi, T. Kamachi, K. Kato, T. Kato and K. Yoshizawa,
1653.
Eur. J. Org. Chem., 2011, 2011, 4113–4120.
26 | Green Chem., 2020, 22, 22–27
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