Recent Advances in Copper-Catalyzed N-O Cleavage Strategy

  • Lu Lei ,
  • Chengjing Li ,
  • Dongliang Mo
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  • a State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, Guilin 541004
    b College of Chemistry & Environment Engineering, Baise University, Baise, Guangxi 533000

Received date: 2019-04-14

  Online published: 2019-07-03

Supported by

the "Overseas 100 Talents Program" of Guangxi Higher Education, the "One Thousand Young and Middle-Aged College and University Backbone Teachers Cultivation Program" of Guangxi Zhuang Autonomous Region, and the Natural Science Foundation of Guangxi Zhuang Autonomous Region(2016GXNSFFA380005)

Abstract

N-O bond cleavage is one of the most efficient and powerful strategies to introduce N-or O-functional groups into molecules in organic synthesis. Copper catalyst, as the abundant in earth and inexpensive advantages has been widely used to construct C-N and C-O bond. Furthermore, N-O bond cleavage has been successfully applied in the total synthesis of natural products and pharmaceuticals. The new development of copper-catalyzed N-O bond cleavage and its application in the total synthesis of natural products and pharmaceuticals in recent years have been summarized.

Cite this article

Lu Lei , Chengjing Li , Dongliang Mo . Recent Advances in Copper-Catalyzed N-O Cleavage Strategy[J]. Chinese Journal of Organic Chemistry, 2019 , 39(11) : 2989 -3012 . DOI: 10.6023/cjoc201904037

References

[1] Bolotin D. S. Bokach N. A. Demakova M. Y. Kukushkin V. Y. Chem. Rev. 2017 117 13039.
[2] (a) Jiao, Y.-X.; Ma, X.-P.; Su, G.-F.; Mo, D.-L. Synthesis. 2017, 49, 933.
[2] (b) Chen, N.; Xie, J. Org. Biomol. Chem. 2016, 14, 11028.
[3] (a) Shi, W.-M.; Ma, X.-P.; Su, G.-F.; Mo, D.-L. Org. Chem. Front. 2016, 3, 116.
[3] (b) Murahashi, S.-I.; Imada, Y. Chem. Rev. 2019, 119, 4684.
[4] Lu D.-F. Zhu C.-L. Jia Z.-X. Xu H. J. Am. Chem. Soc. 2014 136 13186.
[5] Senadi G. C. Lu T.-Y. Dhandabani G. K. Wang J.-J. Org. Lett. 2017 19 1172.
[6] Neely J. M. Rovis T. J. Am. Chem. Soc. 2013 135 66.
[7] Yeom H.-S. Shin S. Acc. Chem. Res. 2014 47 966.
[8] (a) Yao, C.-Z.; Xiao, Z.-F.; Liu, J.; Ning, X.-S.; Kang, Y.-B. Org. Lett. 2014, 16, 2498.
[8] (b) Kumar, C. V. S.; Ramana, C. V. Org. Lett. 2015, 17, 2870.
[9] (a) Zhou, J.; Shi, J.; Qi, Z.; Li, X.; Xu, H. E.; Yi, W. ACS Catal. 2015, 5, 6999.
[9] (b) Xia, J.; Yang, X.; Li, Y.; Li, X. Org. Lett. 2017, 19, 3242.
[10] Nakamura I. Sato Y. Terada M. J. Am. Chem. Soc. 2009 131 4198.
[11] Sivakumar G. Vijeta A. Jeganmohan M. Chem. Eur. J. 2016 22 5899.
[12] Liu X.-G. Gao H. Zhang S.-S. Li Q. Wang H. ACS Catal. 2017 7 5078.
[13] (a) Yang, H.-B.; Pathipati, S. R.; Selander, N. ACS Catal. 2017, 7, 8441.
[13] (b) Ding, D.; Wang, C. ACS Catal. 2018, 8, 111324.
[14] Tang X. Wu W. Zeng W. Jiang H. Acc. Chem. Res. 2018 51 1092.
[15] (a) Ma, X.-P.; Liu, F.-P.; Mo, D.-L. Chin. J. Org. Chem. 2017, 37, 1069 (in Chinese).
[15] (b) Lu, Q.; Yi, H.; Lei, A. Acta Chim. Sinica 2015, 73, 1245.
[15] (c) Zhang, J.; Lu, Q.; Liu, C.; Lei, A. Chin. J. Org. Chem. 2015, 35, 743 (in Chinese).
[16] (a) Ma, D.; Cai, Q. Acc. Chem. Res. 2008, 41, 1450.
[16] (b) McCann, S. D.; Stahl, S. S. Acc. Chem. Res. 2015, 48, 1756.
[17] Dong X. Liu Q. Dong Y. Liu H. Chem. Eur. J. 2017 23 2481.
[18] Jiang H. Yang J. Tang X. Li J. Wu W. J. Org. Chem. 2015 80 8763.
[19] Fu Y. Wang P. Guo X. Wu P. Meng X. Chen B. J. Org. Chem. 2016 81 11671.
[20] Tan W. W. Ong Y. J. Yoshikai N. Angew. Chem. Int. Ed. 2017 56 8240.
[21] Bai D. Wang X. Zheng G. Li X. Angew. Chem. Int. Ed. 2018 57 6633.
[22] Jiang H. Yang J. Tang X. Wu W. J. Org. Chem. 2016 81 2053.
[23] Ramaraju A. Chouhan N. K. Ravi O. Sridhar B. Bathula S. R. Eur. J. Org. Chem. 2018 2963.
[24] Huang H. Cai J. Ji X. Xiao F. Chen Y. Deng G.-J. Angew. Chem. Int. Ed. 2016 55 307.
[25] Zhao B. Liang H.-W. Yang J. Yang Z. Wei Y. ACS Catal. 2017 7 5612.
[26] Zhu C. Zhu R. Zeng H. Chen F. Liu C. Wu W. Jiang H. Angew. Chem. Int. Ed. 2017 56 13324.
[27] Yang J. Zhao B. Xi Y. Sun S. Yang Z. Ye Y. Jiang K. Wei Y. Org. Lett. 2018 20 1216.
[28] Xie Y. Li Y. Chen X. Liu Y. Zhang W. Org. Chem. Front. 2018 5 1698.
[29] Dai X.-J. Engl O. D. León T. Buchwald S. L. Angew. Chem. Int. Ed. 2019 58 3407.
[30] Zhao B. Shi Z. Angew. Chem. Int. Ed. 2017 56 12727.
[31] Ai W. Liu Y. Wang Q. Lu Z. Liu Q. Org. Lett. 2018 20 409.
[32] Zhu C. Chen F. Liu C. Zeng H. Yang Z. Wu W. Jiang H. J. Org. Chem. 2018 83 14713.
[33] An Z. Jiang Y. Guan X. Yan R. Chem. Commun. 2018 54 10738.
[34] Wu J. Zhang J.-Y. Gao P. Xu S.-L. Guo L.-N. J. Org. Chem. 2018 83 1046.
[35] He M. Yan Z. Zhu F. Lin S. J. Org. Chem. 2018 83 15438.
[36] Yu X.-Y. Zhao Q.-Q. Chen J. Chen J.-R. Xiao W.-J. Angew. Chem. Int. Ed. 2018 57 15505.
[37] Wang P. Zhao B. Yuan Y. Shi Z. Chem. Commun. 2019 55 1971.
[38] He Y. Lou J. Wu K. Wang H. Yu Z. J. Org. Chem. 2019 84 2178.
[39] Min Q.-Q. Li N. Chen G.-L. Liu F. Org. Chem. Front. 2019 6 1200.
[40] Tang X. Zhu Z. Qi C. Wu W. Jiang H. Org. Lett. 2016 18 180.
[41] Tang X. Yan J. Zhu Z. Zheng M. Wu W. Jiang H. J. Org. Chem. 2016 81 11461.
[42] Zhu Z. Tang X. Cen J. Li J. Wu W. Jiang H. Chem. Commun. 2018 54 3767.
[43] Zhou P. Huang Y. Wu W. Yu W. Li J. Zhu Z. Jiang H. Org. Biomol. Chem. 2019 17 3424.
[44] Liu H. Yan X. Chen C. Liu Q. Xi C. Chem. Commun. 2013 49 5513.
[45] Zhu Z. Tang X. Li J. Li X. Wu W. Deng G. Jiang H. Chem. Commun. 2017 53 3228.
[46] Yang H.-B. Selander N. Org. Biomol. Chem. 2017 15 1771.
[47] Xu L.-L. Wang X. Ma B. Yin M.-X. Lin H.-X. Dai H.-X. Yu J.-Q. Chem. Sci. 2018 9 5160.
[48] Ren Z.-H. Zhao M.-N. Yi Y. Wang Y.-Y. Guan Z.-H. Synthesis 2016 48 1920.
[49] Zhu C. Zeng H. Chen F. Liu C. Zhu R. Wu W. Jiang H. Org. Chem. Front. 2018 5 571.
[50] Ke J. Tang Y. Yi H. Li Y. Cheng Y. Liu C. Lei A. Angew. Chem. Int. Ed. 2015 54 6604.
[51] Reidl T. W. Son J. Wink D. J. Anderson L. L. Angew. Chem. Int. Ed. 2017 56 11579.
[52] He M. Yan Z. Wang W. Zhu F. Lin S. Tetrahedron Lett. 2018 59 3706.
[53] Mo D.-L. Anderson L. L. Angew. Chem. 2013 52 6722.
[54] Yan H. Wang H. Li X. Xin X. Wang C. Wan B. Angew. Chem. Int. Ed. 2015 54 10613.
[55] Wolosewicz K. Michalak M. Adamek J. Furman B. Eur. J. Org. Chem. 2016 2212.
[56] Son J. Kim K. H. Mo D.-L. Wink D. J. Anderson L. L. Angew. Chem. Int. Ed. 2017 56 3059.
[57] Kong Y. Liu Y. Wang B. Li S. Liu L. Chang X. Li J. Adv. Synth. Catal. 2018 360 1240.
[58] Hasegawa M. Nomoto A. Soeta T. Ukaji Y. Chem. Lett. 2017 46 45.
[59] Shen W.-B. Sun Q. Li L. Liu X. Zhou B. Yan J.-Z. Lu X. Ye L.-W. Nat. Commun. 2017 8 1748.
[60] Liu X. Zhang Z.-X. Zhou B. Wang Z.-S. Zheng R.-H. Ye L.-W. Org. Biomol. Chem. 2017 15 10156.
[61] Wang Z. Han M.-Y. Li P. Wang L. Eur. J. Org. Chem. 2018 5954.
[62] Tian Z. Xu J. Liu B. Tan Q. Xu B. Org. Lett. 2018 20 2603.
[63] Zou N. Jiao J.-W. Feng Y. Pan C.-X. Liang C. Su G.-F. Mo D.-L. Org. Lett. 2019 21 481.
[64] Ma X.-P. Li L.-G. Zhao H.-P. Du M. Liang C. Mo D.-L. Org. Lett. 2018 20 4571.
[65] Hu F. Szostak M. Adv. Synth. Catal. 2015 357 2583.
[66] Li L. Tan T.-D. Zhang Y.-Q. Liu X. Ye L.-W. Org. Biomol. Chem. 2017 15 8483.
[67] Li L. Wang H. Yu S. Wang X. Li X. Org. Lett. 2016 18 3662.
[68] Biswas A. Karmakar U. Nandi S. Samanta R. J. Org. Chem. 2017 82 8933.
[69] Guo S. Yang C. J. Buchwald S. L. J. Am. Chem. Soc. 2018 140 15976.
[70] Xie F. Shen B. Li X. Org. Lett. 2018 20 7154.
[71] Wang F. Xu P. Wang S.-Y. Ji S.-J. Org. Lett. 2018 20 2204.
[72] Sheng J. He R. Xue J. Wu C. Qiao J. Chen C. Org. Lett. 2018 20 4458.
[73] Galenko E. E. Novikov M. S. Shakirova F. M. Shakirova J. R. Kornyakov I. V. Bodunov V. A. Khlebnikov A. F. J. Org. Chem. 2019 84 3524.
[74] Nakamura I. Iwata T. Zhang D. Terada M. Org. Lett. 2012 14 206.
[75] Nakamura I. Kudo Y. Terada M. Angew. Chem. Int. Ed. 2013 52 7536.
[76] Nakamera I. Ishida Y. Terada M. Org. Lett. 2014 16 2562.
[77] Zhang D. Nakamura I. Terada M. Org. Lett. 2014 16 5184.
[78] Nakamura I. Onuma T. Zhang D. Terada M. Tetrahedron Lett. 2014 55 1178.
[79] Hazra S. Mondal B. Rahaman H. Roy B. Eur. J. Org. Chem. 2014 2806.
[80] Zhou S. Yang Z. Chen X. Li Y. Zhang L. Fang H. Wang W. Zhu X. Wang S. J. Org. Chem. 2015 80 6323.
[81] Sakae R. Hirano k. Satoh T. Miura M. Angew. Chem. Int. Ed. 2015 54 613.
[82] Sakae R. Hirano K. Miura M. J. Am. Chem. Soc. 2015 137 6460.
[83] Hemric B. N. Shen K. Wang Q. J. Am. Chem. Soc. 2016 138 5813.
[84] Nakamura I. Jo T. Ishida Y. Tashiro H. Terada M. Org. Lett. 2017 19 3059.
[85] Xu Q.-F. Liu Q.-Q. Zhang X. You S.-L. Angew. Chem. Int. Ed. 2018 57 15204.
[86] Ichikawa S. Zhu S. Buchwald S. L. Angew. Chem. Int. Ed. 2018 57 8714.
[87] Ishida Y. Nakamura I. Terada M. J. Am. Chem. Soc. 2018 140 8629.
[88] Wu F. Zhang M. Zhou W. Chen W. Liu M. Wu H. J. Org. Chem. 2018 83 5999.
[89] Yang Z. Jiang K. Chen Y.-C. Wei Y. J. Org. Chem. 2019 84 3725.
[90] Wang Q. Li X. Org. Lett. 2016 18 2102.
[91] ?nie?ek M. Stecko S. Panfil I. Furman B. Chmielewski M. J. Org. Chem. 2013 78 7048.
[92] Diethelm S. Carreira E. M. J. Am. Chem. Soc. 2015 137 6084.
[93] Wang F.-X. Du J.-Y. Wang H.-B. Zhang P.-L. Zhang G.-B. Yu K.-Y. Zhang X.-Z. An X.-T. Cao Y.-X. Fan C.-A. J. Am. Chem. Soc. 2017 139 4282.
[94] Nomura T. Yojoshima T. Fukuyama T. Org. Lett. 2018 20 119.
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