Photocatalysis with g-C3N4 Applied to Organic Synthesis

doi:10.6023/cjoc201609015

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (3): 577-585.DOI: 10.6023/cjoc201609015 Previous Articles Next Articles

REVIEW

g-C₃N₄光催化剂在有机合成中的应用

戴小强, 朱亚波, 许孝良, 翁建全

浙江工业大学化学工程学院杭州 310014

收稿日期:2016-09-13 修回日期:2016-11-02 发布日期:2016-11-17
通讯作者: 翁建全,E-mail:jqweng@zjut.edu.cn E-mail:jqweng@zjut.edu.cn
基金资助:
国家自然科学基金（No.30900959）和浙江省公益性（No.2014C31127）资助项目.

Photocatalysis with g-C₃N₄ Applied to Organic Synthesis

Dai Xiaoqiang, Zhu Yabo, Xu Xiaoliang, Weng Jianquan

College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014

Received:2016-09-13 Revised:2016-11-02 Published:2016-11-17
Contact: 10.6023/cjoc201609015 E-mail:jqweng@zjut.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (No. 30900959) and the Public Project of Zhejiang Province (No. 2014C31127).

Graphite carbon nitride (g-C₃N₄) is a new metal-free photocatalyst. Due to its 2.7 eV band gap which makes it being absorbed in the visible region, as well as unique structure which gives it good photocatalytic activity, g-C₃N₄ has attracted more and more attentions in visible photocatalysis field. The application of photocatalysis with g-C₃N₄ in organic reactions, such as oxidation reaction, reduction reaction, carbon-carbon bond formation, cyclization reaction and other organic reactions, is summarized and its future outlook is also discussed.

Key words: graphite carbon nitride, visible light catalysis, organic reactions

Cite this article

Dai Xiaoqiang, Zhu Yabo, Xu Xiaoliang, Weng Jianquan. Photocatalysis with g-C₃N₄ Applied to Organic Synthesis[J]. Chin. J. Org. Chem., 2017, 37(3): 577-585.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Hoffmann, N. Chem. Rev. 2008, 108, 1052.
[2] Bach, T.; Hehn, J. P. Angew. Chem., Int. Ed. 2011, 50, 1000.
[3] Ciamician, G. Science 1912, 36, 385.
[4] Tan, F.; Xiao, W. J. Acta Chim. Sinica 2015, 73, 85 (in Chinese).(谭芬, 肖文精, 化学学报, 2015, 73, 85.)
[5] Sun, X. Y.; Yu, S. Y. Chin. J. Org. Chem. 2016, 36, 239 (in Chinese).(孙晓阳, 俞寿云, 有机化学, 2016, 36, 239.)
[6] Guan, B. C.; Xu, X. L.; Wang, H.; Li, X. N. Chin. J. Org. Chem. 2016, 36, 1564 (in Chinese).(关保川, 许孝良, 王红, 李小年, 有机化学, 2016, 36, 1564.)
[7] Zuo, X.; Wu, W. l.; Su, W. P. Acta Chim. Sinica 2015, 73, 1298 (in Chinese).(左旋, 吴文亮, 苏伟平, 化学学报, 2015, 73, 1298.)
[8] Fujishima, A.; Hondak, K. Nature 1972, 238, 37.
[9] Kudo, A.; Miseki, Y. Chem. Soc. Rev. 2009, 38, 253.
[10] Chen, X. B.; Shen, S. H.; Guo, L. J.; Mao, S. S. Chem. Rev. 2010, 110, 6503.
[11] Chatterjee, D.; Dasgupta, S. J. Photochem. Photobiol. C 2005, 6, 186.
[12] Habisreutinger, S. N.; Schmidt-Mende, L.; Stolarczyk, J. K. Angew. Chem., Int. Ed. 2013, 52, 7372.
[13] Lang, X. J.; Chen, X. D.; Zhao, J. C. Chem. Soc. Rev. 2014, 43, 473.
[14] Hamada, T.; Ishida, H.; Usui, S.; Watanabe, Y.; Tsumura, K.; Ohkubo, K. J. Chem. Soc., Chem. Commun. 1993, 11, 909.
[15] Su, F. Z.; Mathew, S.; Lipner, G.; Fu, X. Z.; Wang, X. C. J. Am. Chem. Soc. 2011, 331, 195.
[16] Liebig, J. V. Ann. Pharm. 1834, 10, 10.
[17] Goettmann, F.; Fischer, A.; Antonietti, M.; Thomas, A. Angew. Chem., Int. Ed. 2006, 45, 4467.
[18] Goettmann, F.; Fischer, A.; Antonietti, M.; Thomas, A. Chem. Commun. 2006, 43, 4530.
[19] Wang, X. C.; Maeda, K.; Thomas, A.; Takanabe, K.; Xin, G.; Carlsson, J. M.; Domen, K. A.; Antonietti, M. Nat. Mater. 2009, 8, 76.
[20] Cao, S. W.; Low, J. X.; Yu, J. G.; Jaroniec. M. Adv. Mater. 2015, 27, 2150.
[21] Yan, S. C.; Lv, S. B.; Li, Z. S.; Zou, Z. G. Dalton Trans. 2010, 39, 1488.
[22] Chen, D. M.; Wang, K. W.; Xiang, D. G.; Zong, R. L.; Yao, W. Q.; Zhu, Y. F. Appl. Catal. B 2014, 147, 554.
[23] Goettmann, F.; Fischer, A.; Antonietti, M.; Thomas, A. Angew. Chem., Int. Ed. 2006, 45, 4467.
[24] Goettmann, F.; Fischer, A.; Antonietti, M.; Thomas, A. Chem. Commun. 2006, 43, 4530.
[25] Su, F. Z.; Mathew, S. C.; Lipner, G.; Fu, X. Z.; Antonietti, M.; Blechert, S.; Wang, X. C. J. Am. Chem. Soc. 2010, 132, 16299.
[26] Zheng, Z. S.; Zhou, X. S. Chin. J. Chem. 2012, 30, 1683.
[27] Long, B. H.; Ding, Z. X.; Wang, X. C. ChemSusChem 2013, 6, 2074.
[28] Chen, Y.; Zhang, J. S.; Zhang, M. W.; Wang, X. C. Chem. Sci. 2013, 4, 3244.
[29] Xiao, X. Y.; Jiang, J.; Zhang, L. Z. Appl. Catal. B 2013, 142, 487.
[30] Shiraishi, Y.; Kanazawa, S.; Sugano, Y.; Tsukamoto, D.; Sa-kamoto, H.; Ichikawa, S.; Hirai, T. ACS Catal. 2014, 4, 774.
[31] Dai, X.; Xie, M. L; Meng, S. G.; Fu, X. L.; Chen, S. F. Appl. Catal. B 2014, 158, 382.
[32] Zhang, P. F.; Deng, J.; Mao, J. Y.; Li, H. R.; Wang, Y. Chin. J. Catal. 2015, 36, 1580.
[33] Verma, S.; Nasir Baig, R. B.; Nadagouda, M. N.; Varma, R. S. ACS Sustainable Chem. Eng. 2016, 4, 1094.
[34] Chen, X. F.; Zhang, J. S.; Fu, X. Z.; Antonietti, M.; Wang, X. C. J. Am. Chem. Soc. 2009, 131, 11658.
[35] Ding, Z. X.; Chen, X. F.; Antonietti, M.; Wang, X. C. ChemSus-Chem 2011, 4, 274.
[36] Shiravand, G.; Badiei, A.; Ziarani, G. M.; Jafarabadi, M.; Hamzehloo, M. Chin. J. Catal. 2012, 33, 1347.
[37] Zhang, P. F.; Gong, Y. T.; Li, H. R.; Chen, Z. R.; Wang, Y. RSC Adv. 2013, 3, 5121.
[38] Ye, X. J.; Cui, Y. J.; Wang, X. C. ChemSusChem 2014, 7, 738.
[39] Ye, X. J.; Cui, Y. J.; Qiu, X. Q.; Wang, X. C. Appl. Catal. B 2014, 152, 383.
[40] Su, F. Z.; Mathew, S. C.; Möhlmann, L.; Antonietti, M.; Wang, X. C.; Blechert, S. Angew. Chem., Int. Ed. 2011, 50, 657.
[41] Zhang, P. F.; Wang, Y.; Yao, J.; Wang, C. M.; Yan, C.; Antonietti, M.; Li, H. R. Adv. Synth. Catal. 2011, 353, 1447.
[42] Zhang, P. F.; Wang, Y.; Li, H. R.; Antonietti, M. Green Chem. 2012, 14, 1904.
[43] Zhang, H. Y.; Liu, W. J.; Fu, M. L.; Cen, J. H. Lin, J. X.; Cao, H. Appl. Catal. A 2013, 468, 184.
[44] Wang, H.; Jiang, S. L.; Chen, S. C.; Li, D. D.; Zhang, X. D.; Shao, W.; Sun, X. S.; Xie, J. F.; Zhao, Z.; Zhang, Q.; Tian, Y. P.; Xie, Y. Adv. Mater. 2016, 28, 6940.
[45] Xu, X. L.; Mao, R. J.; Li, X. N. CN 105330688, 2016[Chem. Abstr. 2016, 164, 350027].
[46] Mao, J.; Peng, T. Y.; Zhang, X. H.; Li, K.; Ye, L. Q.; Zan, L. Catal. Sci. Technol. 2013, 3, 1253.
[47] Niu, P.; Yang, Y. Q.; Yu, J. C.; Liu, G.; Cheng, H. M. Chem. Commun. 2014, 50, 10837.
[48] Yu, W. L.; Xu, D. F.; Peng, T. Y. J. Mater. Chem. A 2015, 3, 19936.
[49] Ong, W. J.; Tan, L. L.; Chai, S. P.; Yong, S. T. Chem. Commun. 2015, 51, 858.
[50] Huang, Q.; Yu, J. G.; Cao, S. W.; Cui, C.; Cheng, B. Appl. Surf. Sci. 2015, 358, 350.
[51] Sagara, N.; Kamimura, S.; Tsubota, T.; Ohno, T. Appl. Catal. B 2016, 192, 193.
[52] Zhang, X. J.; Wang, L.; Du, Q. C.; Wang, Z. Y.; Ma, S. G.; Yu, M. J. Colloid Interface Sci. 2016, 464, 89.
[53] Ohon, T.; Murakami, N.; Koyanagi, T.; Yang, Y. J. CO2 Util. 2014, 6, 17.
[54] Gang, M. Y.; He, G. W.; Li, Z.; Cao, K. T.; Li, Z. Y.; Yin, Y. H.; Wu, H.; Jiang, Z. Y. J. Membr. Sci. 2016, 507, 1.
[55] Nasir Baig, R. B.; Verma, S.; Varma, R. S.; Nadagouda, M. N. ACS Sustainable Chem. Eng. 2016, 4, 1661.
[56] Li, D. S.; Hu, F. C.; Hou, D. F.; Qiao, X. Q.; Tian, F. Y. CN 105642329, 2016[Chem. Abstr. 2016, 165, 108778].
[57] Kiskan, B.; Zhang, J. S.; Wang, X. C.; Antonietti, M.; Yagci, Y. ACS Macro Lett. 2012, 1, 546.
[58] Möhlmann, L.; Baar, M.; Rieß, J.; Antonietti, M.; Wang, X. C.; Blechert, S. Adv. Synth. Catal. 2012, 354, 1909.
[59] Moehlmann, L.; Blechert, S. Adv. Synth. Catal. 2014, 356, 2825.
[60] Baar, M.; Blechert, S. Chem. Eur. J. 2015, 21, 526.
[61] Song, L. M.; Zhang, S. J.; Wu, X. Q.; Tian, H. F.; Wei, Q. W. Ind. Eng. Chem. Res. 2012, 51, 9510.
[62] Ding, Z. X.; Chen, X. F.; Antonietti, M.; Wang, X. C. ChemSus-Chem 2011, 4, 274.
[63] Wo?nica, M.; Chaoui, N.; Taabache, S.; Blechert, S. Chem. Eur. J. 2014, 20, 14624.
[64] Song, T.; Zhou, B.; Peng, G. W.; Zhang, Q. B.; Wu, L. Z.; Liu, Q.; Wang, Y. Chem. Eur. J. 2014, 20, 678.
[65] Martin, D. J.; Reardon, P. J. T.; Moniz, S. J. A.; Tang, J. W. J. Am. Chem. Soc. 2014, 136, 12568.
[66] Liu, J.; Huang, J. H.; Zhou, H.; Antonietti, M. ACS. Appl. Mater. Interfaces 2014, 6, 8434.
[67] Kong, H. J.; Won, D. H.; Kim, J.; Woo, S. I. Chem. Mater. 2016, 28, 1318.
[68] Hu, X. F.; Ji, H. H.; Chang, F.; Luo, Y. M. Catal. Today 2014, 224, 34.
[69] Yang, J.; Chen, H. H.; Gao, J. H.; Yan, T. T.; Zhou, F. Y.; Cui, S. H.; Bi, W. T. Mater. Lett. 2016, 164, 183.
[70] Chen, X. X.; Huang, X. T.; Yi, Z. G. Chem. Eur. J. 2014, 20, 17590.
[71] Chi, F. L.; Zhou, G. D.; Song, B.; Lv, Y. H.; Ran, S. L. CN 105148975, 2015[Chem. Abstr. 2015, 164, 119258].
[72] Ma, S. S.; Xue, J. J.; Zhou, Y. M.; Zhang, Z. W.; Cai, Z. L.; Zhu, D. B.; Liang, S. RSC Adv. 2015, 5, 64976.
[73] Liu, Z. R.; Zheng, H.; Yang, H. X.; Hao, L.; Wen, L.; Xu, T. Z.; Wu, S. Y. RSC Adv. 2016, 6, 54215.
[74] Cui, Y. M.; Li, H. Q.; Miao, H. CN 105195221, 2015[Chem. Abstr. 2015, 164, 119258].
[75] Pan, X. Y.; Chen, X. X.; Yi, Z. G. ACS Appl. Mater. Interfaces 2016, 8, 167060.
[76] Dong, F. Zhao, Z. W.; Sun, Y. J.; Zhang, Y. X.; Yan, S.; Wu, Z. B. Environ. Sci. Technol. 2015, 49, 12432.
[77] Ou, M.; Zhong, Q.; Zhang, S. L.; Yu, L. M. J. Alloys Compd. 2015, 626, 401.
[78] Song, X.; Hu, Y.; Zheng, M. M.; Wei, C. H. Appl. Catal. B 2016, 182, 587.
[79] Zhang, Z. Z.; Xu, M. K.; Ho, W. K.; Zhang, X. W.; Yang, Z. Y.; Wang, X. X. Appl. Catal. B 2016, 184, 174.
[80] Li, Y. H.; Yang, L. P.; Dong, G. H.; Ho, W. K. Molecules 2016, 21, 36.

g-C₃N₄光催化剂在有机合成中的应用

Photocatalysis with g-C₃N₄ Applied to Organic Synthesis

PDF

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 9

Recommended Articles

Metrics

Comments

[1]	Yanhua Gao, Yinpan Zhang, Yan Zhang, Tao Song, Yong Yang. Visible-Light-Induced Aerobic Oxidation of Alcohols over Surface Oxygen Vacancies-Enriched Nb₂O₅ [J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2572-2579.
[2]	Jinxiao Zhao, Tonghui Wei, Sen Ke, Yi Li. Visible Light-Catalyzed Synthesis of Difluoroalkylated Polycyclic Indoles [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 1102-1114.
[3]	Jiajie Zhu, Yi Wan, Qiyang Yuan, Jinlian Wei, Yongqiang Zhang. Research of Visible Light/Lewis Base Dual Catalytic Defluorinative Silylation of Trifluoromethyl-Substituted Alkenes [J]. Chinese Journal of Organic Chemistry, 2023, 43(10): 3623-3634.
[4]	Chengjun Zhao, Zhiqin Bai, Jian He, Qiang Liu. Improving the Efficiency of Sensitized Quinoxlin-2(1H)-ones via Pyrazolylation: Synthesis of Azetidines and Further Ring-Opening Reaction [J]. Chinese Journal of Organic Chemistry, 2022, 42(12): 4300-4314.
[5]	He Zhao, Dongping Cheng, Xiaoliang Xu. Application of α-Aminoalkyl Radical in Visible Light Catalysis [J]. Chinese Journal of Organic Chemistry, 2021, 41(2): 642-660.
[6]	Hao Bingjie, Song Tao, Huang Xiaoyu, Ye Mao, Qian Wenhao. Organic Reactions in Covalent Functionalization of Graphene [J]. Chinese Journal of Organic Chemistry, 2020, 40(10): 3279-3288.
[7]	Li Xiaowei, Zhou Jin, Zhuo Shuping. Recent Progress of Supported N-Heterocyclic Carbene Catalyst in Organic Reactions [J]. Chin. J. Org. Chem., 2016, 36(7): 1484-1500.
[8]	Guan Baochuan, Xu Xiaoliang, Wang Hong, Li Xiaonian. Progress on the Decarboxylation Coupling Reaction Mediated by Visible Light [J]. Chinese Journal of Organic Chemistry, 2016, 36(7): 1564-1571.
[9]	JIANG Huan-Feng, WANG Yu-Gang, LIU Hai-Ling, LIU Peng. Application of Non-Metallic Organocatalysts in OrganicChemistry [J]. Chinese Journal of Organic Chemistry, 2004, 24(12): 1513-1531.

g-C3N4光催化剂在有机合成中的应用