Citation: Yuemin Chen, Yunqi Wu, Guoao Wang, Feihu Cui, Haitao Tang, Yingming Pan. Electricity-driven enantioselective cross-dehydrogenative coupling of two C(sp³)-H bonds enabled by organocatalysis[J]. Chinese Chemical Letters, ;2024, 35(9): 109445. doi: 10.1016/j.cclet.2023.109445 shu

Electricity-driven enantioselective cross-dehydrogenative coupling of two C(sp³)-H bonds enabled by organocatalysis

State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry and Pharmaceutical Sciences of Guangxi Normal University, Guilin 541004, China

httang@gxnu.edu.cn

panym@mailbox.gxnu.edu.cn

Received Date: 13 October 2023
Revised Date: 10 December 2023
Accepted Date: 20 December 2023
Available Online: 28 May 2024

Figures(5)

An efficient and scalable electrochemical asymmetric protocol with metal-free catalysts and even without additional oxidants for the cross-dehydrogenative coupling reaction (CDC) of two C(sp³)-H bonds is reported. A series of aldehydes including natural products and various substrates containing C(sp³)-H bonds including xanthenes, acridines, cycloheptatrienes and even diarylmethane have been shown to undergo asymmetric CDC to afford a series of carbon-carbon bond coupling products with up to 94% yield and 98% ee. Mechanistic studies such as radical clock experiment suggest that the reaction proceeds via nucleophilic attack by enamine under electrochemical conditions.
- Aminocatalysis,
- Electrochemistry,
- Asymmetric catalysis,
- CDC of C(sp³)-H bonds
1. [1]
  Y. Yuan, A. Lei, Acc. Chem. Res. 52 (2019) 3309–3324. doi: 10.1021/acs.accounts.9b00512
2. [2]
  Z. Yang, W. Shi, H. Alhumade, H. Yi, A. Lei, Nat. Synth. 2 (2023) 217–230. doi: 10.1038/s44160-022-00221-2
3. [3]
  J.L. Röckl, D. Pollok, R. Franke, S.R. Waldvogel, Acc. Chem. Res. 53 (2020) 45–61. doi: 10.1021/acs.accounts.9b00511
4. [4]
  W.B. He, S.J. Zhao, J.Y. Chen, et al., Chin. Chem. Lett. 34 (2023) 107640. doi: 10.1016/j.cclet.2022.06.063
5. [5]
  Y.H. Lu, S.Y. Mu, J. Jiang, et al., ChemSusChem 16 (2023) e202300523. doi: 10.1002/cssc.202300523
6. [6]
  H.T. Tang, Y.Z. Pan, Y.M. Pan, Green Chem. 25 (2023) 8313–8327. doi: 10.1039/d3gc02106h
7. [7]
  Y.H. Lu, Z.T. Zhang, H.Y. Wu, et al., Chin. Chem. Lett. 34 (2023) 108036. doi: 10.1016/j.cclet.2022.108036
8. [8]
  X.Q. Zhou, H.T. Tang, F.H. Cui, et al., Green Chem. 25 (2023) 5024–5029. doi: 10.1039/d3gc01288c
9. [9]
  J.Y. Chen, C.T. Zhong, Q.W. Gui, et al., Chin. Chem. Lett. 32 (2021) 475–479. doi: 10.1016/j.cclet.2020.09.034
10. [10]
  Z.L. Wu, J.Y. Chen, X.Z. Tian, et al., Chin. Chem. Lett. 33 (2022) 1501–1504. doi: 10.1016/j.cclet.2021.08.071
11. [11]
  Y. Wu, J.Y. Chen, H.R. Liao, et al., Green Synth. Catal. 2 (2021) 233–236. doi: 10.1016/j.gresc.2021.03.006
12. [12]
  I. Kerschgens, A.R. Rovira, R. Sarpong, J. Am. Chem. Soc. 140 (2018) 9810–9813. doi: 10.1021/jacs.8b05832
13. [13]
  X.Y. Dong, Y.F. Zhang, C.L. Ma, et al., Nat. Chem. 11 (2019) 1158–1166. doi: 10.1038/s41557-019-0346-2
14. [14]
  Y. Gao, C. Yang, S. Bai, et al., Chem 6 (2020) 675–688. doi: 10.1016/j.chempr.2019.12.010
15. [15]
  Y.H. Lu, S.Y. Mu, H.X. Li, et al., Green Chem. 25 (2023) 5539. doi: 10.1039/d2gc04906f
16. [16]
  W. Zhang, L. Lu, W. Zhang, et al., Nature 604 (2022) 292–297. doi: 10.1038/s41586-022-04540-4
17. [17]
  B. Zhang, Y. Gao, Y. Hioki, et al., Nature 606 (2022) 313–318. doi: 10.1038/s41586-022-04691-4
18. [18]
  M.Y.S. Ibrahim, G.R. Cumming, D.V.R. Gonzalez, et al., J. Am. Chem. Soc. 145 (2023) 17023–17028. doi: 10.1021/jacs.3c07313
19. [19]
  S. Mu, H. Lia, Z. Wu, et al., Chin. J. Org. Chem. 42 (2022) 4292. doi: 10.6023/cjoc202211002
20. [20]
  T. Tian, Z. Li, C.J. Li, Green Chem. 23 (2021) 6789–6862. doi: 10.1039/d1gc01871j
21. [21]
  K. Matcha, A.P. Antonchick, Angew. Chem. Int. Ed. 52 (2013) 2082–2086. doi: 10.1002/anie.201208851
22. [22]
  Z.J. Wu, H.C. Xu, Angew. Chem. Int. Ed. 56 (2017) 4734–4738. doi: 10.1002/anie.201701329
23. [23]
  S.A. Girard, T. Knauber, C.J. Li, Angew. Chem. Int. Ed. 53 (2014) 74–100. doi: 10.1002/anie.201304268
24. [24]
  E. Larionov, M.M. Mastandrea, M.A. Pericàs, ACS Catal. 7 (2017) 7008–7013. doi: 10.1021/acscatal.7b02659
25. [25]
  A.K. Bagdi, M. Rahman, D. Bhattacherjee, et al., Green Chem. 22 (2020) 6632–6681. doi: 10.1039/d0gc02437f
26. [26]
  J. Blom, G.J. Reyes-Rodríguez, H.N. Tobiesen, et al., Angew. Chem. Int. Ed. 58 (2019) 17856–17862. doi: 10.1002/anie.201911793
27. [27]
  B. Zhang, S.K. Xiang, L.H. Zhang, Y. Cui, N. Jiao, Org. Lett. 13 (2011) 5212–5215. doi: 10.1021/ol202090a
28. [28]
  Q. Chen, X. Wang, G. Yu, C. Wen, Y. Huo, Org. Chem. Front. 5 (2018) 2652–2656. doi: 10.1039/c8qo00740c
29. [29]
  W. Cao, X. Liu, R. Peng, et al., Chem. Commun. 49 (2013) 3470–3472. doi: 10.1039/c3cc41315b
30. [30]
  Y. Wei, J. Tang, X. Cong, X. Zeng, Green Chem. 15 (2013) 3165–3169. doi: 10.1039/c3gc41403e
31. [31]
  Y. Zhang, K.B. Teuscher, H. Ji, Chem. Sci. 7 (2016) 2111–2118. doi: 10.1039/C5SC03640B
32. [32]
  H.Y. Song, F. Xiao, J. Jiang, et al., Chin. Chem. Lett. 34 (2023) 108509. doi: 10.1016/j.cclet.2023.108509
33. [33]
  Q. Zhang, K. Liang, C. Guo, Angew. Chem. Int. Ed. 61 (2022) e202210632. doi: 10.1002/anie.202210632
34. [34]
  K. Yamamoto, M. Kuriyama, O. Onomura, Curr. Opin. Electrochem. 28 (2021) 100714. doi: 10.1016/j.coelec.2021.100714
35. [35]
  J.C. Siu, N. Fu, S. Lin, Acc. Chem. Res. 53 (2020) 547–560. doi: 10.1021/acs.accounts.9b00529
36. [36]
  K.J. Jiao, Z.M. Li, X.T. Xu, et al., Org. Chem. Front. 5 (2018) 2244–2248. doi: 10.1039/c8qo00507a
37. [37]
  X. Wang, S. Wu, Y. Zhong, et al., Chin. Chem. Lett. 34 (2023) 107537. doi: 10.1016/j.cclet.2022.05.051
38. [38]
  T.V. Münchow, S. Dana, Y. Xu, B. Yuan, L. Ackermann, Science 379 (2023) 1036–1042. doi: 10.1126/science.adg2866
39. [39]
  H.Y. Zhou, H.T. Tang, W.M. He, Chin. J. Catal. 46 (2023) 4–10. doi: 10.1016/S1872-2067(22)64197-4
40. [40]
  X.L. Lai, M. Chen, Y. Wang, J. Song, H.C. Xu, J. Am. Chem. Soc. 144 (2022) 20201–20206. doi: 10.1021/jacs.2c09050
41. [41]
  P. Zhou, W. Li, J. Lan, T. Zhu, Nat. Commun. 13 (2022) 3827. doi: 10.1038/s41467-022-31453-7
42. [42]
  C.H. Ou, Y.M. Pan, H.T. Tang, Sci. China Chem. 65 (2022) 1873–1878. doi: 10.1007/s11426-022-1360-3
43. [43]
  A. Vega-Peñaloza, S. Paria, M. Bonchio, L. Dell' Amico, X. Companyó, ACS Catal. 9 (2019) 6058–6072. doi: 10.1021/acscatal.9b01556
44. [44]
  L. Zhu, D. Wang, Z. Jia, et al., ACS Catal. 8 (2018) 5466–5484. doi: 10.1021/acscatal.8b01263
45. [45]
  F. An, B. Maji, E. Min, A.R. Ofial, H. Mayr, J. Am. Chem. Soc. 142 (2020) 1526–1547. doi: 10.1021/jacs.9b11877
46. [46]
  A.E. Allen, D.W.C. Macmillan, J. Am. Chem. Soc. 132 (2010) 4986–4987. doi: 10.1021/ja100748y
47. [47]
  B. List, R.A. Lerner, C.F. Barbas Ⅲ, J. Am. Chem. Soc. 122 (2000) 2395–2396. doi: 10.1021/ja994280y
48. [48]
  E. Arceo, I.D. Jurberg, A. Álvarez-Fernández, P. Melchiorre, Nat. Chem. 5 (2013) 750–756. doi: 10.1038/nchem.1727
49. [49]
  S. Mondal, F. Dumur, D. Gigmes, et al., Chem. Rev. 122 (2022) 5842–5976. doi: 10.1021/acs.chemrev.1c00582
50. [50]
  S. Mukherjee, J.W. Yang, S. Hoffmann, B. List, Chem. Rev. 107 (2007) 5471–5569. doi: 10.1021/cr0684016
51. [51]
  D.W.C. Macmillan, Nature 455 (2008) 304–308. doi: 10.1038/nature07367
52. [52]
  Z.H. Wang, P.S. Gao, X. Wang, et al., J. Am. Chem. Soc. 143 (2021) 15599–15605. doi: 10.1021/jacs.1c08671
53. [53]
  N. Fu, L. Li, Q. Yang, S. Luo, Org. Lett. 19 (2017) 2122–2125. doi: 10.1021/acs.orglett.7b00746
54. [54]
  F.Y. Lu, Y.J. Chen, Y. Chen, et al., Chem. Commun. 56 (2020) 623–626. doi: 10.1039/c9cc09178e
55. [55]
  J. Jiang, K.L. Wang, X. Li, et al., Chin. Chem. Lett. 34 (2023) 108699. doi: 10.1016/j.cclet.2023.108699
56. [56]
  X.H. Ho, S. Mho, H. Kang, H.Y. Jang, Eur, J. Org. Chem. 2010 (2010) 4436–4441. doi: 10.1002/ejoc.201000453
57. [57]
  K.L. Jensen, P.T. Franke, L.T. Nielsen, K. Daasbjerg, K.A. Jørgensen, Angew. Chem. Int. Ed. 49 (2010) 129–133. doi: 10.1002/anie.200904754
58. [58]
  M.D. Palkowitz, G. Laudadio, S. Kolb, et al., J. Am. Chem. Soc. 144 (2022) 17709–17720. doi: 10.1021/jacs.2c08006
59. [59]
  K. Zhou, Y. Yu, Y.M. Lin, Y. Li, L. Gong, Green Chem. 22 (2020) 4597–4603. doi: 10.1039/d0gc00262c
60. [60]
  J.F. Van Humbeck, S.P. Simonovich, R.R. Knowles, D.W.C. Macmillan, J. Am. Chem. Soc. 132 (2010) 10012–10014. doi: 10.1021/ja1043006
1. [1]
  Zhirong Yang , Shan Wang , Ming Jiang , Gengchen Li , Long Li , Fangzhi Peng , Zhihui Shao . One stone three birds: Ni-catalyzed asymmetric allenylic substitution of allenic ethers, hydroalkylation of 1,3-enynes and double alkylation of enynyl ethers. Chinese Chemical Letters, 2024, 35(8): 109518-. doi: 10.1016/j.cclet.2024.109518
2. [2]
  Yan-Bo Li , Yi Li , Liang Yin . Copper(Ⅰ)-catalyzed diastereodivergent construction of vicinal P-chiral and C-chiral centers facilitated by dual "soft-soft" interaction. Chinese Chemical Letters, 2024, 35(7): 109294-. doi: 10.1016/j.cclet.2023.109294
3. [3]
  Xue Xin , Qiming Qu , Islam E. Khalil , Yuting Huang , Mo Wei , Jie Chen , Weina Zhang , Fengwei Huo , Wenjing Liu . Hetero-phase zirconia encapsulated with Au nanoparticles for boosting electrocatalytic nitrogen reduction. Chinese Chemical Letters, 2024, 35(5): 108654-. doi: 10.1016/j.cclet.2023.108654
4. [4]
  Zixuan Guo , Xiaoshuai Han , Chunmei Zhang , Shuijian He , Kunming Liu , Jiapeng Hu , Weisen Yang , Shaoju Jian , Shaohua Jiang , Gaigai Duan . Activation of biomass-derived porous carbon for supercapacitors: A review. Chinese Chemical Letters, 2024, 35(7): 109007-. doi: 10.1016/j.cclet.2023.109007
5. [5]
  Qiang Cao , Xue-Feng Cheng , Jia Wang , Chang Zhou , Liu-Jun Yang , Guan Wang , Dong-Yun Chen , Jing-Hui He , Jian-Mei Lu . Graphene from microwave-initiated upcycling of waste polyethylene for electrocatalytic reduction of chloramphenicol. Chinese Chemical Letters, 2024, 35(4): 108759-. doi: 10.1016/j.cclet.2023.108759
6. [6]
  Xingfen Huang , Jiefeng Zhu , Chuan He . Catalytic enantioselective N-silylation of sulfoximine. Chinese Chemical Letters, 2024, 35(4): 108783-. doi: 10.1016/j.cclet.2023.108783
7. [7]
  Haoran Shi , Jiaxin Wang , Yuqin Zhu , Hongyang Li , Guodong Ju , Lanlan Zhang , Chao Wang . Highly selective α-C(sp³)-H arylation of alkenyl amides via nickel chain-walking catalysis. Chinese Chemical Letters, 2024, 35(7): 109333-. doi: 10.1016/j.cclet.2023.109333
8. [8]
  Lei Wan , Yizhou Tong , Xi Lu , Yao Fu . Cobalt-catalyzed reductive alkynylation to construct C(sp)-C(sp³) and C(sp)-C(sp²) bonds. Chinese Chemical Letters, 2024, 35(7): 109283-. doi: 10.1016/j.cclet.2023.109283
9. [9]
  Tong Li , Leping Pan , Yan Zhang , Jihu Su , Kai Li , Kuiliang Li , Hu Chen , Qi Sun , Zhiyong Wang . Electrochemical construction of 2,5-diaryloxazoles via N–H and C(sp³)-H functionalization. Chinese Chemical Letters, 2024, 35(4): 108897-. doi: 10.1016/j.cclet.2023.108897
10. [10]
  Yujia Shi , Yan Qiao , Pengfei Xie , Miaomiao Tian , Xingwei Li , Junbiao Chang , Bingxian Liu . Rhodium-catalyzed enantioselective in situ C(sp³)−H heteroarylation by a desymmetrization approach. Chinese Chemical Letters, 2024, 35(10): 109544-. doi: 10.1016/j.cclet.2024.109544
11. [11]
  Yi Luo , Lin Dong . Multicomponent remote C(sp²)-H bond addition by Ru catalysis: An efficient access to the alkylarylation of 2H-imidazoles. Chinese Chemical Letters, 2024, 35(10): 109648-. doi: 10.1016/j.cclet.2024.109648
12. [12]
  Zhen Liu , Zhi-Yuan Ren , Chen Yang , Xiangyi Shao , Li Chen , Xin Li . Asymmetric alkenylation reaction of benzoxazinones with diarylethylenes catalyzed by B(C₆F₅)₃/chiral phosphoric acid. Chinese Chemical Letters, 2024, 35(5): 108939-. doi: 10.1016/j.cclet.2023.108939
13. [13]
  Conghui Wang , Lei Xu , Zhenhua Jia , Teck-Peng Loh . Recent applications of macrocycles in supramolecular catalysis. Chinese Chemical Letters, 2024, 35(4): 109075-. doi: 10.1016/j.cclet.2023.109075
14. [14]
  Wei Chen , Pieter Cnudde . A minireview to ketene chemistry in zeolite catalysis. Chinese Journal of Structural Chemistry, 2024, 43(11): 100412-100412. doi: 10.1016/j.cjsc.2024.100412
15. [15]
  Long Jin , Jian Han , Dongmei Fang , Min Wang , Jian Liao . Pd-catalyzed asymmetric carbonyl alkynylation: Synthesis of axial chiral ynones. Chinese Chemical Letters, 2024, 35(6): 109212-. doi: 10.1016/j.cclet.2023.109212
16. [16]
  Pei Cao , Yilan Wang , Lejian Yu , Miao Wang , Liming Zhao , Xu Hou . Dynamic asymmetric mechanical responsive carbon nanotube fiber for ionic logic gate. Chinese Chemical Letters, 2024, 35(6): 109421-. doi: 10.1016/j.cclet.2023.109421
17. [17]
  Yu Mao , Yilin Liu , Xiaochen Wang , Shengyang Ni , Yi Pan , Yi Wang . Acylfluorination of enynes via phosphine and silver catalysis. Chinese Chemical Letters, 2024, 35(8): 109443-. doi: 10.1016/j.cclet.2023.109443
18. [18]
  Ning LI , Siyu DU , Xueyi WANG , Hui YANG , Tao ZHOU , Zhimin GUAN , Peng FEI , Hongfang MA , Shang JIANG . Preparation and efficient catalysis for olefins epoxidation of a polyoxovanadate-based hybrid. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 799-808. doi: 10.11862/CJIC.20230372
19. [19]
  Uttam Pandurang Patil . Porous carbon catalysis in sustainable synthesis of functional heterocycles: An overview. Chinese Chemical Letters, 2024, 35(8): 109472-. doi: 10.1016/j.cclet.2023.109472
20. [20]
  Liliang Chu , Xiaoyan Zhang , Jianing Li , Xuelei Deng , Miao Wu , Ya Cheng , Weiping Zhu , Xuhong Qian , Yunpeng Bai . Continuous-flow synthesis of polysubstituted γ-butyrolactones via enzymatic cascade catalysis. Chinese Chemical Letters, 2024, 35(4): 108896-. doi: 10.1016/j.cclet.2023.108896

Get Citation

PDF

XML

Metrics

PDF Downloads(2)
Abstract views(151)
HTML views(7)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

Electricity-driven enantioselective cross-dehydrogenative coupling of two C(sp3)-H bonds enabled by organocatalysis

Metrics

通讯作者: 陈斌, bchen63@163.com

Electricity-driven enantioselective cross-dehydrogenative coupling of two C(sp³)-H bonds enabled by organocatalysis