研究论文

氮杂环卡宾(NHC)/银(I)共催化合成2-氧代-2-芳乙基芳甲酸酯

  • 成立 ,
  • 王文蓉 ,
  • 孙玉倩 ,
  • 李团结 ,
  • 于晨侠 ,
  • 姚昌盛
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  • 1 江苏师范大学化学与材料科学学院 江苏省功能材料绿色合成重点实验室 江苏徐州 221116

收稿日期: 2020-08-20

  修回日期: 2020-10-13

  网络出版日期: 2020-12-24

基金资助

国家自然科学基金(2177020721); 国家自然科学基金(21871113); 江苏高等学校自然科学基金(17KJA150003)

N-Heterocyclic Carbene (NHC)/Ag(I) Co-catalyzed Synthesis of 2-Oxo-2-arylethyl Aryl Formates

  • Li Cheng ,
  • Wenrong Wang ,
  • Yuqian Sun ,
  • Tuanjie Li ,
  • Chenxia Yu ,
  • Changsheng Yao
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  • 1 Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou, Jiangsu 221116
* Corresponding authors. E-mail: ;

Received date: 2020-08-20

  Revised date: 2020-10-13

  Online published: 2020-12-24

Supported by

National Science Foundation of China(2177020721); National Science Foundation of China(21871113); Natural Science Foundation of the Jiangsu Higher Education Institution(17KJA150003)

摘要

在氮杂环卡宾(NHC)/银(I)的共催化下, 以芳醛和(溴乙炔)苯及其衍生物为原料实现了2-氧代-2-芳乙基芳甲酸酯高效合成. 该方法具有底物范围广、原料简单易得、操作简便等优点, 为α-酰氧基羰基衍生物的简捷合成提供了新思路.

本文引用格式

成立 , 王文蓉 , 孙玉倩 , 李团结 , 于晨侠 , 姚昌盛 . 氮杂环卡宾(NHC)/银(I)共催化合成2-氧代-2-芳乙基芳甲酸酯[J]. 有机化学, 2021 , 41(4) : 1607 -1613 . DOI: 10.6023/cjoc202008035

Abstract

An N-heterocyclic carbene (NHC)/Ag(I) co-catayzed efficient synthesis of 2-oxo-2-arylethyl aryl formates was realized by the reaction of aryl aldehydes with (bromoethynyl)benzenes. This method features broad substrate scope, ready availability of starting materials and operational simplicity, which gives an alternative access to α-acyloxycarbonyl derivatives.

参考文献

[1]
Lin, L.; Mulholland, N.; Wu, Q.-Y.; Beattie, D.; Huang, S.-W.; Irwin, D.; Clough, J.; Gu, Y.-C.; Yang, G.-F. J. Agric. Food Chem. 2012, 60,4480.
[2]
Wang, X.; Sena Filho, J.G.; Hoover, A.R.; King, J.B.; Ellis, T.K.; Powell, D.R.; Cichewicz, R.H. J. Nat. Prod. 2010, 73,942.
[3]
Wang, H.; Wang, Y.; Wang, W.; Fu, P.; Liu, P.; Zhu, W. J. Nat. Prod. 2011, 74,2014.
[4]
(a) Sabbah, D.A.; Saada, M.; Khalaf, R.A.; Bardaweel, S.; Sweidan, K.; Al-Qirim, T.; Al-Zughier, A.; Halim, H.A.; Sheikh, G.A. Bioorg. Med. Chem. Lett. 2015, 25,3120.
[4]
(b) Che, Y.; Wen, D.; Huang, Z.; Huang, M.; Luo, Y.; Liu, B.; Lu, H.; Wu, Y.; Peng, Y.; Zhang, J. Bioorg. Med. Chem. Lett. 2012, 22,6867.
[5]
Dai, L.; Yu, S.; Xiong, W.; Chen, Z.; Xu, T.; Shao, Y.; Chen, J. Adv. Synth. Catal. 2020, 362,1893.
[6]
Kim, S.H.; Jang, M.; Moon, D.Y.; Park, B.S. Tetrahedron Lett. 2018, 59,4245.
[7]
Arai, M.A.; Kofuji, Y.; Tanaka, Y.; Yanase, N.; Yamaku, K.; Fuentes, R.G.; Karmakar, U.K.; Ishibashi, M. Org. Biomol. Chem. 2016, 14,3061.
[8]
(a) Funk, P.; Motyka, K.; D?ubák, P.; Znojek, P.; Gurská, S.; Kusz, J.; McMaster, C.; Hajdúch, M.; Soural, M. RSC Adv. 2015, 5,48861.
[8]
(b) Kadri?, J.; Motyka, K.; D?ubák, P.; Hajdúch, M.; Soural, M. Tetrahedron Lett. 2014, 55,3592.
[9]
(a) Prasad, P.K.; Reddi, R.N.; Arumugam, S. Org. Biomol. Chem. 2018, 16,9334.
[9]
(b) Zhou, X.; Ma, H.; Cao, J.; Liu, X.; Huang, G.; Org. Biomol. Chem. 2016, 14,10070.
[9]
(c) Zhu, Y.; Zheng, Y.; Song, W.; Wei, B.; Xuan, L. Tetrahedron Lett. 2018, 59,368.
[9]
(d) Zhu, M.; Wei, W.; Yang, D.; Cui, H.; Sun, X.; Wang, H. Org. Biomol. Chem. 2016, 14,10998.
[10]
(a) Kreibich, M.; Gemander, M.; Peter, D.; Yadav, D.; Koning, C.; Fernandes, M.; Green, I.; van Otterlo, W.; Brückner, R. Eur. J. Org. Chem. 2020, 19,2929.
[10]
(b) Liu, L.; Feng, S.; Li, C. ACS Sustainable Chem. Eng. 2016, 4,6754.
[10]
(c) Hu, Y.; Chen, J.; Le, Z.G.; Chen, Z.C.; Zheng, Q.G. Chin. Chem. Lett. 2005, 16,903.
[10]
(d) Wang, X.; Li, G.; Yang, Y.; Jiang, J.; Feng, Z.; Zhang, P. Chin. Chem. Lett. 2020, 31,711.
[11]
Mondal, B.; Sahoo, S.C.; Pan, S.C. Eur. J. Org. Chem. 2015, 14,3135.
[12]
Wang, J.-L.; Wang, J.-Q.; He, L.-N.; Dou, X.-Y.; Wu, F. Green Chem. 2008, 10,1218.
[13]
Ji, K.; Zhao, Y.; Zhang, L. Angew. Chem. Int. Ed. 2013, 52,6508.
[14]
Mu, Y.; Chen, Y.; Gao, Y.; Sun, J.; Iqbal, Z.; Wan, Y.; Yang, M.; Yang, Z.; Tang, D. ChemistrySelect 2020, 5,1705.
[15]
Tian, L.; Guo, Y.; Wei, L.; Wan, J.-P.; Sheng, S. Asian J. Org. Chem. 2019, 8,1484.
[16]
Li, J.; Yang, Z.; Yang, T.; Yi, J.; Zhou, C. New J. Chem. 2018, 42,1581.
[17]
Chen, C.; Liu, W.; Zhou, P.; Liu, H. RSC Adv. 2017, 7,20394.
[18]
Tan, L.; Chen, C.; Liu, W. Beilstein J. Org. Chem. 2017, 13,1079.
[19]
(a) Flanigan, D.M.; Romanov-Michailidis, F.; White, N.A.; Rovis, T. Chem. Rev. 2015, 115,9307.
[19]
(b) Enders, D.; Niemeier, O.; Henseler, A. Chem. Rev. 2007, 107,5606.
[19]
(c) Wang, Z.; Li, R.; Qian, H.; Yao, C. Chin. J. Org. Chem. 2019, 39,2075. (in Chinese)
[19]
( 王占林, 李如一, 钱辉旻, 姚昌盛, 有机化学, 2019, 39,2075.)
[19]
(d) Yao, C.; Xiao, Z.; Liu, R.; Li, T.; Jiao, W.; Yu, C. Chem. Eur. J. 2013, 19,456.
[19]
(e) Li, S.; Yang, W.; Luo, X.; Yao, C. Chin. J. Org. Chem. 2019, 39,1404. (in Chinese)
[19]
( 李莎, 杨雯涵, 罗鲜, 姚昌盛, 有机化学, 2019, 39,1404.)
[19]
(f) Li, S.; Xu, J.; Luo, X.; Yang, W.; Yao, C. Chin. J. Org. Chem. 2020, 40,470. (in Chinese)
[19]
( 李莎, 徐嘉煜, 罗鲜, 杨雯涵, 姚昌盛, 有机化学, 2020, 40,470.)
[19]
(g) Zhang, Y.; Xing, F.; Feng, Z.; Du, G.; Gu, C.; He, L. Chin. J. Org. Chem. 2020, 40,1608. (in Chinese)
[19]
( 张阳, 邢芬, 冯泽男, 杜广芬, 顾承志, 何林, 有机化学, 2020, 40,1608.)
[19]
(h) Wang, A.; Xiao, Y.; Zhou, Y.; Xu, J.; Liu, H. Chin. J. Org. Chem. 2017, 37,2590. (in Chinese)
[19]
( 王翱, 肖永龙, 周宇, 徐进宜, 柳红, 有机化学, 2017, 37,2590.)
[19]
(i) Qu, M.; He, J. Chin. J. Org. Chem. 2011, 31,1388. (in Chinese)
[19]
( 屈孟男, 何金梅, 有机化学, 2011, 31,1388.)
[20]
Reddi, R.N.; Malekar, P.V.; Sudalai, A. Org. Biomol. Chem. 2013, 11,6477.
[21]
Reddi, R.N.; Gontala, A.; Prasad, P.K.; Sudalai, A. Asian J. Org. Chem. 2016, 5,48.
[22]
Forte, G.; Chiarotto, I.; Inesi, A.; Loreto, M.A.; Feroci, M. Adv. Synth. Catal. 2014, 356,1773.
[23]
Lu, H.; Liu, J.-Y.; Li, H.-Y.; Xu, P.-F. Acta Chim. Sinica 2018, 76,831. (in Chinese)
[23]
( 鲁鸿, 刘金宇, 李红玉, 许鹏飞, 化学学报, 2018, 76,831.)
[24]
Nemoto, T.; Fukuda, T.; Hamada, Y. Tetrahedron Lett. 2006, 47,4365.
[25]
(a) Namitharan, K.; Zhu, T.; Cheng, J.; Zheng, P.; Li, X.; Yang, S.; Song, B.-A.; Chi, Y.R. Nat. Commun. 2014, 5,3982.
[25]
(b) Chen, J.; Yuan, P.; Wang, L.; Huang, Y. J. Am. Chem. Soc. 2017, 139,7045.
[26]
DiRocco, D.A.; Rovis, T. J. Am. Chem. Soc. 2012, 134,8094.
[27]
Chen, Z.-W.; Ye, D.-N.; Ye, M.; Zhou, Z.-G.; Li, S.-H.; Liu, L.-X. Tetrahedron Lett. 2014, 55,1373.
[28]
Jia, Y.; Li, T.; Yu, C.; Jiang, B.; Yao, C. Org. Biomol. Chem. 2016, 14,1982.
[29]
(a) Liu, Y.K.; Li, R.; Yue, L.; Li, B.J.; Chen, Y.C.; Wu, Y.; Ding, L.S. Org. Lett. 2006, 8,1521.
[29]
(b) Xia, Z.-H.; Dai, L.; Gao, Z.-H.; Ye, S. Chem. Commun. 2020, 56,1525.
[29]
(c) Gao, Z.-H.; Xia, Z.-H.; Dai, L.; Ye, S. Adv. Synth. Catal. 2020, 362,1819.
[30]
Liao, L.; Zhang, H.; Zhao, X. ACS Catal. 2018, 8,6745.
[31]
Hu, Y.; Chen, J.; Le, Z.G.; Chen, Z.C.; Zheng, Q.G. Chin. Chem. Lett. 2005, 16,903.
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