α-酮酸、异腈和水的电化学三组分合成α-酮酰胺
收稿日期: 2021-11-04
修回日期: 2021-12-09
网络出版日期: 2021-12-15
基金资助
国家自然科学基金(21545010); 湖南省自然科学基金(2020JJ4599); 湖南省科技创新计划(2021RC5028)
Electrochemical Multicomponent Synthesis of α-Ketoamides from α-Oxocarboxylic Acids, Isocyanides and Water
Received date: 2021-11-04
Revised date: 2021-12-09
Online published: 2021-12-15
Supported by
National Natural Science Foundation of China(21545010); Natural Science Foundation of Hunan Province(2020JJ4599); Science and Technology Innovation Program of Hunan Province(2021RC5028)
吴红谕 , 于贤勇 , 曹忠 . α-酮酸、异腈和水的电化学三组分合成α-酮酰胺[J]. 有机化学, 2021 , 41(12) : 4712 -4717 . DOI: 10.6023/cjoc202111010
Electrochemical organic synthesis is considered as an environmentally benign method because it employs traceless electrons as redox agents, thereby avoiding the need for chemical oxidants. The electrochemical decarboxylative acylation of isocyanides and relay hydration reaction for the synthesis of α-ketoamides was developed. This reaction can be carried out under mild conditions in the absence of a chemical oxidant and a transition-metal catalyst.
[1] | (a) Zhang, B.; Studer, A. Chem. Soc. Rev. 2015, 44, 3505. |
[1] | (b) Song, B.; Xu, B. Chem. Soc. Rev. 2017, 46, 1103. |
[1] | (c) Wei, W.; Bao, P.; Yue, H.; Liu, S.; Wang, L.; Li, Y.; Yang, D. Org. Lett. 2018, 20, 5291. |
[1] | (d) Bao, W.-H.; Wang, Z.; Tang, X.; Zhang, Y.-F.; Tan, J.-X.; Zhu, Q.; Cao, Z.; Lin, Y.-W.; He, W.-M. Chin. Chem. Lett. 2019, 30, 2259. |
[1] | (e) Mao, Z.-Y.; Nie, X.-D.; Feng, Y.-M.; Si, C.-M.; Wei, B.-G.; Lin, G.-Q. Chem. Commun. 2021, 57, 9248. |
[1] | (f) Liu, Y.; Chen, X.-L.; Li, X.-Y.; Zhu, S.-S.; Li, S.-J.; Song, Y.; Qu, L.-B.; Yu, B. J. Am. Chem. Soc. 2021, 143, 964. |
[1] | (g) He, Y.; Wang, Y.-C.; Hu, K.; Xu, X.-L.; Wang, H.-S.; Pan, Y.-M. J. Org. Chem. 2016, 81, 11813. |
[1] | (h) He, Y.; Wang, Y.; Liang, X.; Huang, B.; Wang, H.; Pan, Y.-M., Org. Lett. 2018, 20, 7117. |
[1] | (i) Cao, M.; Liu, L.; Tang, S.; Peng, Z.; Wang, Y. Adv. Synth. Catal. 2019, 361, 1887. |
[1] | (j) Cao, M.; Fang, Y.-L.; Wang, Y.-C.; Xu, X.-J.; Xi, Z.-W.; Tang, S., ACS Comb. Sci. 2020, 22, 268. |
[1] | (k) Cao, M.; Teng, Q.-H.; Xi, Z.-W.; Liu, L.-Q.; Gu, R.-Y.; Wang, Y.-C. Org. Biomol. Chem. 2020, 18, 655. |
[2] | (a) De Risi, C.; Pollini, G. P.; Zanirato, V. Chem. Rev. 2016, 116, 3241. |
[2] | (b) Rao, Y. S.; Latha, D. S.; Devunuri, N.; Almansour, A. I.; Arumugam, N.; Yaragorla, S. Eur. J. Org. Chem. 2020, 2020, 4134. |
[2] | (c) Mishra, A. A.; Chaurasia, S. R.; Bhanage, B. M. New J. Chem. 2020, 44, 10578. |
[3] | (a) Chen, J.-C.; Uang, B.-J.; Lyu, P.-C.; Chang, J.-Y.; Liu, K.-J.; Kuo, C.-C.; Hsieh, H.-P.; Wang, H.-C.; Cheng, C.-S.; Chang, Y.-H.; Chang, M. D.-T.; Chang, W.-S. W.; Lin, C.-C. J. Med. Chem. 2010, 53, 4545. |
[3] | (b) Steuer, C.; Gege, C.; Fischl, W.; Heinonen, K. H.; Bartenschlager, R.; Klein, C. D. Biorg. Med. Chem. 2011, 19, 4067. |
[3] | (c) Sridhar, S. N. C.; Ginson, G.; Venkataramana Reddy, P. O.; Tantak, M. P.; Kumar, D.; Paul, A. T. Biorg. Med. Chem. 2017, 25, 609. |
[4] | (a) Du, F.-T.; Ji, J.-X. Chem. Sci. 2012, 3, 460. |
[4] | (b) Kumar, D.; Vemula, S. R.; Cook, G. R. ACS Catal. 2016, 6, 4920. |
[4] | (c) Majumdar, B.; Sarma, D.; Bhattacharya, T.; Sarma, T. K. ACS Sustainable Chem. Eng. 2017, 5, 9286. |
[4] | (d) Chen, J.-Y.; Wu, H.-Y.; Gui, Q.-W.; Han, X.-R.; Wu, Y.; Du, K.; Cao, Z.; Lin, Y.-W.; He, W.-M. Org. Lett. 2020, 22, 2206. |
[5] | (a) Penteado, F.; Lopes, E. F.; Alves, D.; Perin, G.; Jacob, R. G.; Lenardão, E. J. Chem. Rev. 2019, 119, 7113. |
[5] | (b) Zhang, J.; Wu, M.; Fan, J.; Xu, Q.; Xie, M. Chem. Commun. 2019, 55, 8102. |
[5] | (c) Shi, J.; Wei, W. Chin. J. Org. Chem. 2020, 40, 2170. (in Chinese) |
[5] | ( 时建伟, 魏伟, 有机化学, 2020, 40, 2170.) |
[5] | (d) 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. |
[5] | (e) Xie, K.; Jiang, M.; Chen, X.; Lv, Q.; Yu, B. Chin. J. Org. Chem. 2021, 41, 4575. (in Chinese) |
[5] | ( 谢坤宸, 江铭轩, 陈晓岚, 吕琪妍, 於兵, 有机化学, 2021, 41, 4575.) |
[5] | (f) 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. |
[6] | (a) Mamillapalli, N. C.; Sekar, G. Chem.-Eur. J. 2015, 21, 18584. |
[6] | (b) Muthukumar, A.; Sekar, G. J. Org. Chem. 2018, 83, 8827. |
[7] | Agarwal, R.; Liao, Y.; Lin, D.-J.; Yang, Z.-X.; Lai, C.-F.; Chen, C.-T. Org. Chem. Front. 2020, 7, 2505. |
[8] | Zhu, Z.; Lv, X.; Anesini, J. E.; Seidel, D. Org. Lett. 2017, 19, 6424. |
[9] | Lv, Y.; Bao, P.; Yue, H.; Li, J.-S.; Wei, W. Green Chem. 2019, 21, 6051. |
[10] | (a) Jiang, Y.; Xu, K.; Zeng, C. Chem. Rev. 2018, 118, 4485. |
[10] | (b) Tang, H.-T.; Jia, J.-S.; Pan, Y.-M. Org. Biomol. Chem. 2020, 18, 5315. |
[10] | (c) Li, M.; Wang, R.; Hao, W.; Jiang, B. Chin. J. Org. Chem. 2020, 40, 1540. (in Chinese) |
[10] | ( 李梦帆, 王榕, 郝文娟, 姜波, 有机化学, 2020, 40, 1540.) |
[10] | (d) Cheng, X. Chin. J. Org. Chem. 2020, 40, 2600. (in Chinese) |
[10] | ( 程旭, 有机化学, 2020, 40, 2600.) |
[10] | (e) Yuan, Y.; Yang, J.; Lei, A. Chem. Soc. Rev. 2021, 50, 10058. |
[10] | (f) Chen, J.-Y.; Zhong, C.-T.; Gui, Q.-W.; Zhou, Y.-M.; Fang, Y.-Y.; Liu, K.-J.; Lin, Y.-W.; Cao, Z.; He, W.-M. Chin. Chem. Lett. 2021, 32, 475. |
[10] | (g) Ye, Z.; Zhang, F. Chin. J. Org. Chem. 2021, 41, 241. (in Chinese) |
[10] | ( 叶增辉, 张逢质, 有机化学, 2021, 41, 241.) |
[10] | (h) Wu, Y.; Chen, J.-Y.; Ning, J.; Jiang, X.; Deng, J.; Deng, Y.; Xu, R.; He, W.-M. Green Chem. 2021, 23, 3950. |
[10] | (i) Chen, N.; Lai, X.; Xu, H. Chin. J. Org. Chem. 2021, 40, 2592. (in Chinese) |
[10] | ( 陈娜, 赖小丽, 徐海超, 有机化学, 2021, 40, 2592.) |
[10] | (j) Jiang, J.; Wang, Z.; He, W.-M. Chin. Chem. Lett. 2021, 32, 1591. |
[10] | (k) Tang, H.; Pan, Y. Chin. J. Org. Chem. 2021, 41, 435. (in Chinese) |
[10] | ( 唐海涛, 潘英明, 有机化学, 2021, 41, 435.) |
[10] | (l) Yi, R.-N.; Wu, Z.-L.; Ouyang, W.-T.; Wang, W.-F.; He, W.-M., Tetrahedron Lett. 2021, 77, 153257. |
[10] | (m) Zhang, M.; Zhao, P.; Yuan, H.; Zhang, A. a.; Zhang, W.; Zheng, L.; Wu, D.; Liu, L. Chin. J. Org. Chem. 2021, 41, 669. (in Chinese) |
[10] | ( 张明亮, 赵聘, 袁浩, 张安安, 张文宇, 郑琳琳, 吴冬青, 刘澜涛, 有机化学, 2021, 41, 669.) |
[10] | (n) Sun, K.; Xiao, F.; Yu, B.; He, W.-M. Chin. J. Catal. 2021, 42, 1921. |
[10] | (o) Yang, Z.; Yu, Y.; Lai, L.; Zhou, L.; Ye, K.; Chen, F.-E. Green Synth. Catal. 2021, 2, 19. |
[11] | (a) Chen, D.; Sun, Y.; Dong, D.; Han, Q.; Wang, Z. Chin. J. Org. Chem. 2020, 40, 4267. (in Chinese) |
[11] | ( 陈德茂, 孙媛媛, 董道青, 韩晴晴, 王祖利, 有机化学, 2020, 40, 4267.) |
[11] | (b) Gan, Z.; Li, G.; Yan, Q.; Deng, W.; Jiang, Y.-Y.; Yang, D. Green Chem. 2020, 22, 2956. |
[11] | (c) Wang, L.; Zhang, M.; Zhang, Y.; Liu, Q.; Zhao, X.; Li, J.-S.; Luo, Z.; Wei, W. Chin. Chem. Lett. 2020, 31, 67. |
[11] | (d) Li, W.; He, W. Chin. J. Org. Chem. 2021, 41, 4528. (in Chinese) |
[11] | ( 李文艺, 何卫民, 有机化学, 2021, 41, 4528.) |
[11] | (e) Zeng, F.-L.; Zhu, H.-L.; Chen, X.-L.; Qu, L.-B.; Yu, B. Green Chem. 2021, 23, 3677. |
[11] | (f) 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. |
[11] | (g) Wang, B.; Zou, L.; Wang, L.; Sun, M.; Li, P. Chin. Chem. Lett. 2021, 32, 1229. |
[11] | (h) Yi, R.; He, W. Chin. J. Org. Chem. 2021, 41, 1267. (in Chinese) |
[11] | ( 易荣楠, 何卫民, 有机化学, 2021, 41, 1267.) |
[11] | (i) Jin, W.; Liu, C. Chin. J. Org. Chem. 2021, 41, 2148. (in Chinese) |
[11] | ( 金伟伟, 刘晨江, 有机化学, 2021, 41, 2148.) |
[12] | (a) Quinn, R. K.; Schmidt, V. A.; Alexanian, E. J. Chem. Sci. 2013, 4, 4030. |
[12] | (b) Wang, Q.-Q.; Xu, K.; Jiang, Y.-Y.; Liu, Y.-G.; Sun, B.-G.; Zeng, C.-C. Org. Lett. 2017, 19, 5517. |
[13] | Huang, J.; Liang, B.; Chen, X.; Liu, Y.; Li, Y.; Liang, J.; Zhu, W.; Tang, X.; Li, Y.; Zhu, Z. Org. Biomol. Chem. 2021, 19, 4783. |
[14] | Zhang, C.; Zong, X.; Zhang, L.; Jiao, N., Org. Lett. 2012, 14, 3280. |
[15] | Zhang, Y.-K.; Wang, B. Eur. J. Org. Chem. 2019, 2019, 5732. |
/
〈 |
|
〉 |