Chinese Journal of Organic Chemistry >
Application of α-Keto Acids in Metal-Free Photocatalysis
Received date: 2021-09-04
Revised date: 2021-10-13
Online published: 2021-10-21
Supported by
National Natural Science Foundation of China(21971224); National Natural Science Foundation of China(22171249); Innovation and Entrepreneurship Training Program(S202110459196); Innovation and Entrepreneurship Training Program(2021cxcy197); Top Undergraduates Program of Zhengzhou University
As a carboxylic acid, α-keto acid can be used as an acylating reagent by decarboxylation in organic synthesis. However, traditional methods often need transition metal catalysts or high temperatures, which limits the application of α-keto acid to a certain extent. In recent years, organic transformations induced by visible light have attracted extensive attention due to its mild conditions and simple operations. Herein, the recent advances of metal-free photocatalytic application of α-keto acids are summarized, which mainly include acylation reactions and cyclization reactions.
Key words: α-keto acid; visible light; metal-free catalysis; acylation
Kunchen Xie , Mingxuan Jiang , Xiaolan Chen , Qiyan Lü , Bing Yu . Application of α-Keto Acids in Metal-Free Photocatalysis[J]. Chinese Journal of Organic Chemistry, 2021 , 41(12) : 4575 -4587 . DOI: 10.6023/cjoc202109008
[1] | Ruan, L.; Chen, C.; Zhang, X.; Sun, J. Chin. J. Org. Chem. 2018, 38, 3155. (in Chinese) |
[1] | ( 阮利衡, 陈春欣, 张晓欣, 孙京, 有机化学, 2018, 38, 3155.) |
[2] | Penteado, F.; Lopes, E. F.; Alves, D.; Perin, G.; Jacob, R. G.; Lenardao, E. J. Chem. Rev. 2019, 119, 7113. |
[3] | Wang, L.; Zhang, M.; Zhang, Y.; Liu, Q.; Zhao, X.; Li, J.-S.; Luo, Z.; Wei, W. Chin. Chem. Lett. 2020, 31, 67. |
[4] | Gui, Q.-W.; Teng, F.; Li, Z.-C.; Xiong, Z.-Y.; Jin, X.-F.; Lin, Y.-W.; Cao, Z.; He, W.-M. Chin. Chem. Lett. 2021, 32, 1907. |
[5] | He, F.-S.; Xie, S.; Yao, Y.; Wu, J. Chin. Chem. Lett. 2020, 31, 3065. |
[6] | Du, L.; Li, T. Chin. J. Org. Chem. 2020, 40, 140. (in Chinese) |
[6] | ( 杜琳琳, 李铁生, 有机化学, 2020, 40, 140.) |
[7] | Liu, J.; Xing, X.-N.; Huang, J.-H.; Lu, L.-Q.; Xiao, W.-J. Chem. Sci. 2020, 11, 10605. |
[8] | Yu, X.-Y.; Chen, J.-R.; Xiao, W.-J. Chem. Rev. 2021, 121, 506. |
[9] | Lu, J.; Li, L.; He, X.-K.; Xu, G.-Y.; Xuan, J. Chin. J. Chem. 2021, 39, 1646. |
[10] | Chen, Y.; Lu, L.-Q.; Yu, D.-G.; Zhu, C.-J.; Xiao, W.-J. Sci. China: Chem. 2019, 62, 24. |
[11] | Gan, Z.; Li, G.; Yang, X.; Yan, Q.; Xu, G.; Li, G.; Jiang, Y.-Y.; Yang, D. Sci. China: Chem. 2020, 63, 1652. |
[12] | Gan, Z.; Li, G.; Yan, Q.; Deng, W.; Jiang, Y.-Y.; Yang, D. Green Chem. 2020, 22, 2956. |
[13] | Lü, Q.; Yu, B. J. Liaocheng Univ. (Nat. Sci. Ed.) 2019, 32, 28. (in Chinese) |
[13] | ( 吕琪妍, 於兵, 聊城大学学报(自然科学版), 2019, 32, 28.) |
[14] | Ren, L.; Ran, M.; He, J.; Qian, Y.; Yao, Q. Chin. J. Org. Chem. 2019, 39, 1583. (in Chinese) |
[14] | ( 任林静, 冉茂刚, 何佳芯, 钱燕, 姚秋丽, 有机化学, 2019, 39, 1583.) |
[15] | Chen, J.; Li, Y.; Mei, L.; Wu, H. Chin. J. Org. Chem. 2019, 39, 3040. (in Chinese) |
[15] | ( 陈锦杨, 李玉涵, 梅兰, 吴红谕, 有机化学, 2019, 39, 3040.) |
[16] | Chen, D.; Liu, J.; Zhang, X.; Jiang, H.; Li, J. Chin. J. Org. Chem. 2019, 39, 3353. (in Chinese) |
[16] | ( 陈丹, 刘剑沉, 张馨元, 蒋合众, 李加洪, 有机化学, 2019, 39, 3353.) |
[17] | Yuan, X.; Yang, G.; Yu, B. Chin. J. Org. Chem. 2020, 40, 3620. (in Chinese) |
[17] | ( 袁晓亚, 杨国平, 於兵, 有机化学, 2020, 40, 3620.) |
[18] | Wang, C.; Zhou, L.; Yang, K.; Zhang, F.; Song, Q. Chin. J. Chem. 2021, 39, 1825. |
[19] | Liu, T.; Qu, C.; Xie, J.; Zhu, C. Chin. J. Org. Chem. 2019, 39, 1613. (in Chinese) |
[19] | ( 刘涛, 屈川华, 谢劲, 朱成建, 有机化学, 2019, 39, 1613.) |
[20] | Chen, F.; Chen, H.; Wu, Q.; Luo, S. Chin. J. Org. Chem. 2020, 40, 339. (in Chinese) |
[20] | ( 陈锋, 陈浩, 吴庆安, 罗书平, 有机化学, 2020, 40, 339.) |
[21] | Zhou, R.; Ma, L.; Yang, X.; Cao, J. Org. Chem. Front. 2021, 8, 426. |
[22] | Lu, F.-D.; He, G.-F.; Lu, L.-Q.; Xiao, W.-J. Green Chem. 2021, 23, 5379. |
[23] | Lang, Y.; Li, C.-J.; Zeng, H. Org. Chem. Front. 2021, 8, 3594. |
[24] | Meng, N.; Lv, Y.; Liu, Q.; Liu, R.; Zhao, X.; Wei, W. Chin. Chem. Lett. 2021, 32, 258. |
[25] | Wang, L.; Bao, P.; Liu, W.; Liu, S.; Hu, C.; Yue, H.; Yang, D.; Wei, W. Chin. J. Org. Chem. 2018, 38, 3189. (in Chinese) |
[25] | ( 王雷雷, 鲍鹏丽, 刘维伟, 刘思彤, 胡昌松, 岳会兰, 杨道山, 魏伟, 有机化学, 2018, 38, 3189.) |
[26] | Liu, J.; Liu, Q.; Yi, H.; Qin, C.; Bai, R.; Qi, X.; Lan, Y.; Lei, A. Angew. Chem., Int. Ed. 2014, 53, 502. |
[27] | Wang, H.; Xie, F.; Qi, Z.; Li, X. Org. Lett. 2015, 17, 920. |
[28] | Tan, H.; Li, H.; Ji, W.; Wang, L. Angew. Chem., Int. Ed. 2015, 54, 8374. |
[29] | Shi, Q.; Li, P.; Zhu, X.; Wang, L. Green Chem. 2016, 18, 4916. |
[30] | Pawar, G. G.; Robert, F.; Grau, E.; Cramail, H.; Landais, Y. Chem. Commun. 2018, 54, 9337. |
[31] | Lv, Y.; Bao, P.; Yue, H.; Li, J.-S.; Wei, W. Green Chem. 2019, 21, 6051. |
[32] | Bao, P.; Liu, F.; Lv, Y.; Yue, H.; Li, J.-S.; Wei, W. Org. Chem. Front. 2020, 7, 492. |
[33] | Yang, J.; Song, M.; Zhou, H.; Wang, G.; Ma, B.; Qi, Y.; Huo, C. Org. Lett. 2020, 22, 8407. |
[34] | Zhu, D.-L.; Wu, Q.; Young, D. J.; Wang, H.; Ren, Z.-G.; Li, H.-X. Org. Lett. 2020, 22, 6832. |
[35] | Guillemard, L.; Colobert, F.; Wencel-Delord, J. Adv. Synth. Catal. 2018, 360, 4184. |
[36] | Zhang, X.-Y.; Weng, W.-Z.; Liang, H.; Yang, H.; Zhang, B. Org. Lett. 2018, 20, 4686. |
[37] | Xie, L.-Y.; Bai, Y.-S.; Xu, X.-Q.; Peng, X.; Tang, H.-S.; Huang, Y.; Lin, Y.-W.; Cao, Z.; He, W.-M. Green Chem. 2020, 22, 1720. |
[38] | Shi, J.; Wei, W. Chin. J. Org. Chem. 2020, 40, 2170. (in Chinese) |
[38] | ( 时建伟, 魏伟, 有机化学, 2020, 40, 2170.) |
[39] | Wang, X.; Lei, J.; Li, G.; Meng, J.; Li, C.; Li, J.; Sun, K. Org. Biomol. Chem. 2020, 18, 9762. |
[40] | Yang, G.; Xie, X.; Cheng, M.; Gao, X.; Lin, X.; Li, K.; Cheng, Y.; Liu, Y. Chin. Chem. Lett. 2021, DOI: 10.1016/j.cclet.2021.08.037. |
[41] | Zhang, Z.; Song, X.; Li, G.; Li, X.; Zheng, D.; Zhao, X.; Miao, H.; Zhang, G.; Liu, L. Chin. Chem. Lett. 2021, 32, 1423. |
[42] | Tian, S.; Luo, T.; Zhu, Y.; Wan, J.-P. Chin. Chem. Lett. 2020, 31, 3073. |
[43] | Sun, K.; Xiao, F.; Yu, B.; He, W.-M. Chin. J. Catal. 2021, 42, 1921. |
[44] | Gao, F.; Lü, Q.; Yu, B. J. Liaocheng Univ. (Nat. Sci. Ed.) 2020, 33, 66. (in Chinese) |
[44] | ( 高凡, 吕琪妍, 於兵, 聊城大学学报(自然科学版), 2020, 33, 66.) |
[45] | Shang, Z.-H.; Zhang, Z.-X.; Weng, W.-Z.; Wang, Y.-F.; Cheng, T.-W.; Zhang, Q.-Y.; Song, L.-Q.; Shao, T.-Q.; Liu, K.-X.; Zhu, Y.-P. Adv. Synth. Catal. 2021, 363, 490. |
[46] | Yang, G.; Li, K.; Lin, X.; Li, Y.; Cui, C.; Li, S.; Cheng, Y.; Liu, Y. Chin. J. Chem. 2021, 39, 3017. |
[47] | Mao, P.; Zhu, J.; Yuan, J.; Yang, L.; Xiao, Y.; Zhang, C., Chin. J. Org. Chem. 2019, 39, 1529. (in Chinese) |
[47] | ( 毛璞, 朱军亮, 袁金伟, 杨亮茹, 肖咏梅, 张长森, 有机化学, 2019, 39, 1529.) |
[48] | Monga, A.; Bagchi, S.; Soni, R. K.; Sharma, A. Adv. Synth. Catal. 2020, 362, 2232. |
[49] | Su, Y.; Zhang, R.; Xue, W.; Liu, X.; Zhao, Y.; Wang, K.-H.; Huang, D.; Huo, C.; Hu, Y. Org. Biomol. Chem. 2020, 18, 1940. |
[50] | Zhu, H.-L.; Zeng, F.-L.; Chen, X.-L.; Sun, K.; Li, H.-C.; Yuan, X.-Y.; Qu, L.-B.; Yu, B. Org. Lett. 2021, 23, 2976. |
[51] | Ji, W. Q.; Tan, H.; Wang, M.; Li, P. H.; Wang, L. Chem. Commun. 2016, 52, 1462. |
[52] | Zhao, B.; Zhang, Z.; Ge, Y.; Li, P.; Miao, T.; Wang, L. Org. Chem. Front. 2021, 8, 975. |
[53] | Zhang, J.-J.; Cheng, Y.-B.; Duan, X.-H. Chin. J. Chem. 2017, 35, 311. |
[54] | Jatoi, A. H.; Pawar, G. G.; Robert, F.; Landais, Y. Chem. Commun. 2019, 55, 466. |
/
〈 |
|
〉 |