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Chinese Journal of Organic Chemistry >

2021 , Vol. 41 >Issue 12: 4712 - 4717

DOI: https://doi.org/10.6023/cjoc202111010

ARTICLES

Electrochemical Multicomponent Synthesis of α-Ketoamides from α-Oxocarboxylic Acids, Isocyanides and Water

  • Hongyu Wu ,
  • Xianyong Yu ,
  • Zhong Cao
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  • a Hunan Provincial Key Laboratory of Materials Protection for Electric Power and Transportation, Hunan Provincial Key Laboratory of Cytochemistry, School of Chemistry and Chemical Engineering, Changsha University of Science and Technology, Changsha 410114
    b Key Laboratory of Theoretical Organic Chemistry and Functional Molecule of Ministry of Education, School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan, Hunan 411201
* Corresponding authors. E-mail: ;

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)

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Abstract

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.

Key words： electrochemical synthesis; decarboxylative acylation; hydration reaction; isocyanide; α-ketoamides

Cite this article

Hongyu Wu , Xianyong Yu , Zhong Cao . Electrochemical Multicomponent Synthesis of α-Ketoamides from α-Oxocarboxylic Acids, Isocyanides and Water[J]. Chinese Journal of Organic Chemistry, 2021 , 41(12) : 4712 -4717 . DOI: 10.6023/cjoc202111010

References

[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.
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