REVIEWS

Electron Donor-Acceptor (EDA) Complex-Driven Activation of N-α C—H Bonds

  • Junfeng Yang ,
  • Yanqiu Zhao ,
  • Lei Shi
Expand
  • School of Chemistry, Dalian University of Technology, Dalian 116024

Received date: 2024-06-30

  Revised date: 2024-08-25

  Online published: 2024-09-30

Supported by

National Natural Science Foundation of China(21772195); Fundamental Research Funds for the Central Universities(DUT22QN213)

Abstract

Electron donor-acceptor (EDA) complexes formed by electron donors and electron acceptors are triggering many amazing photochemical reactions. Under visible light irradiation, the EDA complexes undergo a single electron transfer (SET) process, in which electrons are transferred from the donor to the electron acceptor to create free radical anion-cation pairs and initiate subsequent reactions. This strategy does not require an additional photocatalyst under mild reaction conditions with light as an external energy source, making this system compatible well with most substrates. Amines, such as aza-aromatics and aliphatic amines, have been widely used as electron-rich substrates as electron donors in EDA complexes in recent years. Moreover, the reaction intermediates initiated by these EDA complexes are predictable and site-selective, with unique reactive properties at the N-α position after the formation of EDA complexes, and have been used in the synthesis of complex nitrogen-containing organic molecules. The photochemical reactions of nitrogen-containing aromatics and amines as EDA electron donors for the construction of C—X bonds (X=C, N) at the N-α position are reviewed, and an outlook for the development of this field is provided.

Cite this article

Junfeng Yang , Yanqiu Zhao , Lei Shi . Electron Donor-Acceptor (EDA) Complex-Driven Activation of N-α C—H Bonds[J]. Chinese Journal of Organic Chemistry, 2025 , 45(2) : 559 -573 . DOI: 10.6023/cjoc202406050

References

[1]
(a) Akhtar, J.; Khan, A. A.; Ali, Z.; Haider, R.; Yar, M. S. Eur. J. Med. Chem. 2017, 125, 143.
[1]
(b) Nainwal, L. M.; Tasneem, S.; Akhtar, W.; Verma, G.; Khan, M. F.; Parvez, S.; Shaquiquzzaman, M.; Akhter, M.; Alam, M. M. Eur. J. Med. Chem. 2019, 164, 121.
[1]
(c) Bhutani, P.; Joshi, G.; Raja, N.; Bachhav, N.; Rajanna, P. K.; Bhutani, H.; Paul, A. T.; Kumar, R. J. Med. Chem. 2021, 64, 2339.
[1]
(d) Das, P.; Delost, M. D.; Qureshi, M. H.; Smith, D. T.; Njardarson, J. T. J. Med. Chem. 2019, 62, 4265.
[2]
Vitaku, E.; Smith, D. T.; Njardarson, J. T. J. Med. Chem. 2014, 57, 10257.
[3]
(a) Li, C.-J. Acc. Chem. Res. 2009, 42, 335.
[3]
(b) Bagdi, A. K.; Rahman, M.; Bhattacherjee, D.; Zyryanov, G. V.; Ghosh, S.; Chupakhin, O. N.; Hajra, A. Green Chem. 2020, 22, 6632.
[4]
(a) Shi, L.; Xia, W.-J. Chem. Soc. Rev. 2012, 41, 7687.
[4]
(b) Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C. Chem. Rev. 2013, 113, 5322.
[4]
(c) Roero, N. A.; Nicewicz, D. A. Chem. Rev. 2016, 116, 10075.
[5]
(a) Crsenza, G. E. M.; Mazzarella, D.; Melchiorre, P. J. Am. Chem. Soc. 2020, 142, 5461.
[5]
(b) Wortman, A. K.; Stephenson, C. R. J. Chem 2023, 9, 2390.
[6]
Arceo, E.; Jurberg, I. D.; álvarez-Fernández, A.; Melchiorre, P. Nat. Chem. 2013, 5, 750.
[7]
(a) Yang, Z.; Liu, Y.; Cao, K.; Zhang, X.; Jiang, H.; Li, J. Beilstein J. Org. Chem. 2021, 17, 771.
[7]
(b) Tasnim, T.; Ayodele, M. J.; Pitre, S. P. J. Org. Chem. 2022, 87, 10555.
[7]
(c) Volkov, A. A.; Bugaenko, D. I.; Karchava, A. V. ChemCatChem 2024, 16, e202301526.
[8]
(a) Davies, J.; Booth, S. G.; Essafi, S.; Dryfe, R. A. W.; Leonori, D. Angew. Chem., Int. Ed. 2015, 54, 14017.
[8]
(b) Zhang, J.; Li, Y.; Xu, R.; Chen, Y. Angew. Chem.,Int. Ed. 2017, 56, 12619.
[8]
(c) Wu, J.; Grant, P. S.; Li, X.; Noble, A.; Aggarwal, V. K. Angew. Chem., Int. Ed. 2019, 58, 5697.
[8]
(d) Murphy, J. J.; Bastida, D.; Paria, S.; Fagnoni, M.; Melchiorre, P. Nature 2016, 532, 218.
[8]
(e) Bahamonde, A.; Murphy, J. J.; Savarese, M.; Bremond, E.; Cavalli, A.; Melchiorre, P. J. Am. Chem. Soc. 2017, 139, 4559.
[8]
(f) Emmanuel, M. A.; Greenberg, N. R.; Oblinsky, D. G.; Hyster, T. K. Nature 2016, 540, 414.
[8]
(g) Biegasiewicz, K. F.; Cooper, S. J.; Gao, X.; Oblinsky, D. G.; Kim, J. H.; Garfinkle, S. E.; Joyce, L. A.; Sandoval, B. A.; Scholes, G. D.; Hyster, T. K. Science 2019, 364, 1166.
[9]
(a) Proctor, R. S. J.; Phipps, R. J. Angew. Chem., Int. Ed. 2019, 58, 13666.
[9]
(b) Dong, J.; Liu, Y.; Wang, Q. Chin. J. Org. Chem. 2021, 41, 3771 (in Chinese).
[9]
(董建洋, 刘玉秀, 汪清民, 有机化学, 2021, 41, 3771.)
[9]
(c) Meng, W.; Xu, K.; Guo, B.; Zeng, C. Chin. J. Org. Chem. 2021, 41, 2621 (in Chinese).
[9]
(孟薇, 徐坤, 郭兵兵, 曾程初, 有机化学, 2021, 41, 2621.)
[9]
(d) Ghosh, A.; Pyne, P.; Ghosh, S.; Ghosh, D.; Majumder, S.; Hajra, A. Green Chem. 2022, 24, 3056.
[10]
Tobisu, M.; Furukawa, T.; Chatani, N. Chem. Lett. 2013, 42, 1203.
[11]
Mo, F.; Qiu, D.; Zhang, L.; Wang, J. Chem. Rev. 2021, 121, 5741.
[12]
Fürst, M. C. D.; Gans, E.; B?ck, M. J.; Heinrich, M. R. Chem.-Eur. J. 2017, 23, 15312.
[13]
Aganda, K. C. C.; Kim, J.; Lee, A. Org. Biomol. Chem. 2019, 17, 9698.
[14]
(a) Michael, J. P. Nat. Prod. Rep. 2007, 24, 191.
[14]
(b) Movassaghi, M.; Ondrus, A. E.; Chen, B. J. Org. Chem. 2007, 72, 10065.
[15]
Kim, E.; Lee, Y.; Lee, S.; Park, S. B. Acc. Chem. Res. 2015, 48, 538.
[16]
Mane, K. D.; Rupanawar, B. D.; Suryavanshi, G. Eur. J. Org. Chem. 2022, e202200261.
[17]
Kaudukuri, S. R.; Bahamonde, A.; Chatterjee, I.; Jurberg, I. D.; Escudero-Adán, E. C.; Melchiorre, P. Angew. Chem., Int. Ed. 2015, 54, 1485.
[18]
Sharique, M.; Majhi, J.; Dhungana, R. K.; Kammer, L. M.; Krumb, M.; Lipp, A.; Romero, E.; Molander, G. A. Chem. Sci. 2022, 13, 5701.
[19]
Shi, C.; Guo, L.; Gao, H.; Luo, M.; Zhou, X.; Yang, C.; Xia, W. Org. Lett. 2023, 25, 7661.
[20]
Peng, S.; Xie, L.-Y.; Yang, L. Org. Biomol. Chem. 2023, 21, 4109.
[21]
More, D. A.; Shirsath, S. R.; Muthukrishnan, M. J. Org. Chem. 2023, 88, 13339.
[22]
Xu, C.; Shen, F.-Q.; Feng, G.; Jin, J. Org. Lett. 2021, 23, 3913.
[23]
Xie, X.; Guo, X.; Qiao, K.; Shi, L. Org. Biomol. Chem. 2022, 20, 8031.
[24]
Hsu, C.-W.; Sundén, H. Org. Lett. 2018, 20, 2051.
[25]
Runemark, A.; Zacharias, S. C.; Sunde?n, H. J. Org. Chem. 2021, 86, 1901.
[26]
Runemark, A.; Sundén, H. J. Org. Chem. 2022, 87, 1457.
[27]
Tang, M.; Draper, F.; Pham, L. N.; Ho, C. C.; Huang, H.; Sun, J.; Thickett, S. C.; Coote, M. L.; Connell, T. U.; Bissember, A. C. J. Org. Chem. 2024, 89, 2683.
[28]
Zhang, J.; Zhang, Q.-Y.; Tu, P.-F.; Xu, F.-C.; Liang, H. J. Nat. Prod. 2018, 81, 364.
[29]
Li, Z.; Ma, P.; Tan, Y.; Liu, Y.; Gao, M.; Zhang, Y.; Yang, B.; Huang, X.; Gao, Y.; Zhang, J. Green Chem. 2020, 22, 646.
[30]
Zhang, T.; Ren, X.; Wang, B.; Jin, W.; Xia, Y.; Wu, S.; Liu, C.; Zhang, Y. Org. Chem. Front. 2024, 11, 1050.
[31]
Xia, Q.; Li, Y.; Wang, X.; Dai, P.; Deng, H.; Zhang, W. H. Org. Lett. 2020, 22, 7290.
[32]
Ma, P.; Liu, Y.; Chen, L.; Zhao, X.; Yang, B.; Zhang, J. Org. Chem. Front. 2021, 8, 2473.
[33]
Capaldo, L.; Ravelli, D.; Fagnoni, M. Chem. Rev. 2022, 122, 1875.
[34]
Xie, X.; Qiao, K.; Shao, B. R.; Jiang, W.; Shi, L. Org. Lett. 2023, 25, 4264.
[35]
Cong, F.; Zhang, W.; Zhang, G.; Liu, J.; Zhang, Y.; Zhou, C.; Wang, L. Org. Biomol. Chem. 2023, 21, 8910.
[36]
Xia, Q.; Li, Y.; Cheng, L.; Liang, X.; Cao, C.; Dai, P.; Deng, H.; Zhang, W.; Wang, Q. Org. Lett. 2020, 22, 9638.
[37]
Chen, Z.; Zheng, S.; Wang, Z.; Liao, Z.; Yuan, W. ChemPhotoChem 2021, 5, 906.
[38]
Zhao, Y.; Li, L.; Xuan, J. Adv. Synth. Catal. 2023, 365, 110.
[39]
Sui, J.; Yang, Z.; Li, S.; Chen, X.; Zhang, X.; Shen, Q.; Jiang, H.; Li, J. Chin. J. Chem. 2023, 41, 1485.
[40]
Yang, X.; Zhu, Y.; Xie, Z.; Li, Y.; Zhang, Y. Org. Lett. 2020, 22, 1638.
[41]
Wang, C.; Qi, R.; Xue, H.; Shen, Y.; Chang, M.; Chen, Y.; Wang, R.; Xu, Z. Angew. Chem., Int. Ed. 2020, 59, 7461.
[42]
(a) Costantino, G.; Maltoni, K.; Marinozzi, M.; Camaioni, E.; Prezeau, L.; Pin, J.-P.; Pellicciari, R. Bioorg. Med. Chem. 2001, 9, 221.
[42]
(b) Meanwell, N. A. Chem. Res. Toxicol. 2016, 29, 564.
[43]
Dang, X.; Li, Z.; Shang, J.; Zhang, C.; Wang, C.; Xu, Z. Angew. Chem., Int. Ed. 2024, e202400494.
Outlines

/