Citation: Yanqing Zhu, Shuai Chen, Zhen Zhou, Yun He, Zhengli Liu, Yang Liu, Zhang Feng. Iron/B₂pin₂ catalytic system enables the generation of alkyl radicals from inert alkyl C-O bonds for amine synthesis[J]. Chinese Chemical Letters, ;2024, 35(1): 108303. doi: 10.1016/j.cclet.2023.108303 shu

Iron/B₂pin₂ catalytic system enables the generation of alkyl radicals from inert alkyl C-O bonds for amine synthesis

Yanqing Zhu ^a ,
Shuai Chen ^a ,
Zhen Zhou ^a ,
Yun He ^a ,
Zhengli Liu ^{a, c, *,} ,
Yang Liu ^{b, **,} ,
Zhang Feng ^{a, c, *,}

a.
Chongqing Key Laboratory of Natural Product Synthesis and Drug Research, School of Pharmaceutical Sciences, Chongqing University, Chongqing 401331, China
b.
Department of Medicinal Chemistry, School of Pharmacy, Fujian Medical University (FMU), Fuzhou 350005, China
c.
Affiliated Hospital of North Sichuan Medical College and Medical Imaging Key Laboratory of Sichuan Province, Nanchong 637503, China

^**

liuzhengli@cqu.ac.cn

liuyang@fjmu.edu.cn

fengzh@cqu.edu.cn

Received Date: 6 January 2023
Revised Date: 28 February 2023
Accepted Date: 5 March 2023
Available Online: 11 March 2023

Figures(4)

A method for the generation of alkyl radicals from inert alkyl C-O bonds has been developed via an iron/borane reagent/alkoxide catalytic system, which can be employed for the synthesis of amines from nitroarenes with excellent efficiency. Preliminary mechanistic studies reveal that the amine synthesis may be involving a single electron transfer pathway to form alkyl radicals, and the low-valent iron species may be the active intermediates.
- C-N bond formation,
- Reductive amination,
- Borane reagent,
- Iron catalysis,
- Green chemistry
1. [1]
  Q.S. Gu, Z.L. Li, X.Y. Liu, Acc. Chem. Res. 53 (2020) 170-181. doi: 10.1021/acs.accounts.9b00381
2. [2]
  L. Chu, C. Ohta, Z. Zuo, et al., J. Am. Chem. Soc. 136 (2014) 10886–10889. doi: 10.1021/ja505964r
3. [3]
  T. Qin, L.R. Malins, J.T. Edwards, et al., Angew. Chem. Int. Ed. 56 (2017) 260–265. doi: 10.1002/anie.201609662
4. [4]
  J. Wu, P.S. Grant, X. Li, et al., Angew. Chem. Int. Ed. 58 (2019) 5697–5701. doi: 10.1002/anie.201814452
5. [5]
  G.L. Lackner, K.W. Quasdorf, L.E. Overman, J. Am. Chem. Soc. 135 (2013) 15342–15345. doi: 10.1021/ja408971t
6. [6]
  C.C. Nawrat, C.R. Jamison, Y. Slutskyy, et al., J. Am. Chem. Soc. 137 (2015) 11270–11273. doi: 10.1021/jacs.5b07678
7. [7]
  X. Zhang, D.W.C. MacMillan, J. Am. Chem. Soc. 138 (2016) 13862–13865. doi: 10.1021/jacs.6b09533
8. [8]
  Y. Ye, H. Chen, J.L. Sessler, et al., J. Am. Chem. Soc. 141 (2019) 820–824. doi: 10.1021/jacs.8b12801
9. [9]
  M. Gao, D. Sun, H. Gong, Org. Lett. 21 (2019) 1645–1648. doi: 10.1021/acs.orglett.9b00174
10. [10]
  D.H.R. Barton, D. Crich, Tetrahedron Lett. 26 (1985) 757–760. doi: 10.1016/S0040-4039(00)89129-7
11. [11]
  H. Togo, S. Matsubayashi, O. Yamazaki, et al., J. Org. Chem. 65 (2000) 2816–2819. doi: 10.1021/jo991715r
12. [12]
  B.A. Vara, N.R. Patel, G.A. Molander, ACS Catal. 7 (2017) 3955–3959. doi: 10.1021/acscatal.7b00772
13. [13]
  F.W. Friese, A. Studer, Angew. Chem. Int. Ed. 58 (2019) 9561–9564. doi: 10.1002/anie.201904028
14. [14]
  E.C. Ashby, J.N. Argyropoulos, J. Org. Chem. 50 (1985) 3274-3283. doi: 10.1021/jo00218a007
15. [15]
  L.K. Ackerman, L.L. AnkaLufford, M. Naodovic, et al., Chem. Sci. 6 (2015) 1115–1119. doi: 10.1039/C4SC03106G
16. [16]
  K. Komeyama, T. Michiyuki, I. Osaka, ACS Catal. 9 (2019) 9285–9291. doi: 10.1021/acscatal.9b03352
17. [17]
  T. Michiyuki, I. Osaka, K. Komeyama, Chem. Commun. 56 (2020) 1247–1250. doi: 10.1039/c9cc09377j
18. [18]
  K. Komeyama, R. Ohata, S. Kiguchi, et al., Chem. Commun. 53 (2017) 6401–6404. doi: 10.1039/C7CC01932G
19. [19]
  H. Xie, J. Guo, Y.Q. Wang, et al., J. Am. Chem. Soc. 142 (2020) 16787–16794. doi: 10.1021/jacs.0c07492
20. [20]
  X. Zeng, X.J. Dai, H.Q. Yuan, et al., Angew. Chem. Int. Ed. 52 (2013) 3494–3498. doi: 10.1002/anie.201210088
21. [21]
  H. Xie, S. Wang, Y. Wang, et al., ACS Catal. 12 (2022) 1018–1023. doi: 10.1021/acscatal.1c05530
22. [22]
  S.A. Lawrence, Amines: Synthesis Properties and Applications, Cambridge University Press, 2004.
23. [23]
  J.F. Hartwig, Acc. Chem. Res. 41 (2008) 1534–1544. doi: 10.1021/ar800098p
24. [24]
  D.S. Surry, S.L. Buchwald, Angew. Chem. Int. Ed. 47 (2008) 6338–6361. doi: 10.1002/anie.200800497
25. [25]
  W. Zhou, M. Fan, J. Yin, et al., J. Am. Chem. Soc. 137 (2015) 11942–11945. doi: 10.1021/jacs.5b08411
26. [26]
  W. Zhang, J. Xie, B. Rao, et al., J. Org. Chem. 80 (2015) 3504–3511. doi: 10.1021/acs.joc.5b00130
27. [27]
  C.W. Cheung, M.L. Ploege, X. Hu, Nat. Commun. 8 (2017) 14878. doi: 10.1038/ncomms14878
28. [28]
  J. Xiao, Y. He, F. Ye, et al., Chem 4 (2018) 1645–1657. doi: 10.1016/j.chempr.2018.04.008
29. [29]
  C.W. Cheung, M.L. Ploege, X. Hu, Chem. Sci. 9 (2018) 655–659. doi: 10.1039/C7SC03950F
30. [30]
  C.W. Cheung, J.A. Ma, X. Hu, J. Am. Chem. Soc. 140 (2018) 6789–6792. doi: 10.1021/jacs.8b03739
31. [31]
  T.V. Nykaza, J.C. Cooper, G. Li, et al., J. Am. Chem. Soc. 140 (2018) 15200–15205. doi: 10.1021/jacs.8b10769
32. [32]
  S. Suárez-Pantiga, R. Hernández-Ruiz, C. Virumbrales, et al., Angew. Chem. Int. Ed. 58 (2019) 2129–2133. doi: 10.1002/anie.201812806
33. [33]
  D. Formenti, F. Ferretti, F.K. Scharnagl, et al., Chem. Rev. 119 (2019) 2611–2680. doi: 10.1021/acs.chemrev.8b00547
34. [34]
  M.L. Ploeger, A. Daru, J.N. Harvey, et al., ACS Catal. 10 (2020) 2845–2854. doi: 10.1021/acscatal.9b05049
35. [35]
  G. Li, T.V. Nykaza, J.C. Cooper, et al., J. Am. Chem. Soc. 142 (2020) 6786–6799. doi: 10.1021/jacs.0c01666
36. [36]
  H. Song, Z. Yang, C.H. Tung, et al., ACS Catal. 10 (2020) 276–281. doi: 10.1021/acscatal.9b03604
37. [37]
  Y. Ning, S. Wang, M. Li, et al., Nat. Commun. 12 (2021) 4637. doi: 10.1038/s41467-021-24908-w
38. [38]
  G. Li, L. Yang, J.J. Liu, et al., Angew. Chem. Int. Ed. 60 (2021) 5230–5234. doi: 10.1002/anie.202012877
39. [39]
  W. Li, M. Huang, J. Liu, et al., ACS Catal. 11 (2021) 10377–10382. doi: 10.1021/acscatal.1c02956
40. [40]
  X. Guan, H. Zhu, T.G. Driver, ACS Catal. 11 (2021) 12417–12422. doi: 10.1021/acscatal.1c03113
41. [41]
  S. Wang, T. Li, C. Gu, et al., Nat. Commun. 13 (2022) 2432. doi: 10.1038/s41467-022-30176-z
42. [42]
  M. Rauser, C. Ascheberg, M. Niggemann, Angew. Chem. Int. Ed. 56 (2017) 11570–11574. doi: 10.1002/anie.201705356
43. [43]
  M. Rauser, C.R. Eckert, M. Gerbershagen, et al., Angew. Chem. Int. Ed. 58 (2019) 6713–6717. doi: 10.1002/anie.201814197
44. [44]
  J. Gui, C.M. Pan, Y. Jin, et al., Science 348 (2015) 886–891. doi: 10.1126/science.aab0245
45. [45]
  C.W. Cheung, X. Hu, Nat. Commun. 7 (2016) 12494. doi: 10.1038/ncomms12494
46. [46]
  S. Chen, Z. Wang, S. Geng, et al., CCS Chem. 5 (2023) 1674–1685. doi: 10.31635/ccschem.022.202202234
47. [47]
  Q. Wen, S. Chen, C. Shi, et al., Cell. Rep. Phys. Sci. 3 (2022) 100995. doi: 10.1016/j.xcrp.2022.100995
48. [48]
  X. Zeng, Y. Zhang, Z. Liu, et al., Org. Lett. 22 (2020) 2950–2955. doi: 10.1021/acs.orglett.0c00679
49. [49]
  S. Wang, M. Sun, H. Zhang, et al., CCS Chem. 2 (2020) 2164–2173. doi: 10.3390/app10062164
50. [50]
  H. Zhang, E. Wang, S. Geng, et al., Angew. Chem. Int. Ed. 60 (2021) 10211–10218. doi: 10.1002/anie.202100049
51. [51]
  S. Zhou, Y. Pu, Z. Liu, et al., Org. Lett. 23 (2021) 5565–5570. doi: 10.1021/acs.orglett.1c01967
52. [52]
  M. Sun, M. Tao, L. Zhao, et al., Org. Chem. Front. 8 (2021) 5322-5327. doi: 10.1039/d1qo00839k
53. [53]
  J. Jia, X. Zeng, Z. Liu, et al., Org. Lett. 22 (2020) 2816–2821. doi: 10.1021/acs.orglett.0c00809
54. [54]
  J. Zhang, Y. Zhang, S. Geng, et al., Org. Lett. 22 (2020) 2669-2674. doi: 10.1021/acs.orglett.0c00633
55. [55]
  S. Geng, B. Xiong, Y. Zhang, Chem. Commun. 55 (2019) 12699-12702. doi: 10.1039/c9cc06584a
56. [56]
  B. Xiong, X. Zeng, S. Geng, Green Chem. 20 (2018) 4521-4527. doi: 10.1039/c8gc02369g
57. [57]
  A. Piontek, E. Bisz, M. Szostak, Angew. Chem. Int. Ed. 57 (2018) 11116–11128. doi: 10.1002/anie.201800364
58. [58]
  L. Zhang, D. Peng, X. Leng, et al., Angew. Chem. Int. Ed. 52 (2013) 3676–3680. doi: 10.1002/anie.201210347
59. [59]
  B. Cheng, W.B. Liu, Z. Lu, J. Am. Chem. Soc. 140 (2018) 5014–5017. doi: 10.1021/jacs.8b01638
60. [60]
  M.Y. Hu, J. Lian, W. Sun, et al., J. Am. Chem. Soc. 141 (2019) 4579–4583. doi: 10.1021/jacs.9b02127
61. [61]
  W.M. Czaplik, M. Mayer, J. Cvengros, et al., ChemSusChem 2 (2009) 396–417. doi: 10.1002/cssc.200900055
62. [62]
  R.B. Bedford, P.B. Brenner, Top. Organomet. Chem. 50 (2015) 19–46. doi: 10.1007/3418_2015_99
63. [63]
  I. Bauer, H.J. Knölker, Chem. Rev. 115 (2015) 3170–3387. doi: 10.1021/cr500425u
64. [64]
  H. Zhang, Z. Ouyang, Y. Liu, et al., Angew. Chem. Int. Ed. 53 (2014) 8432-8436. doi: 10.1002/anie.201404677
65. [65]
  X. Liu, Y. Chen, K. Li, D. Wang, B. Chen, Chin. J. Chem. 30 (2012) 2285–2291. doi: 10.1002/cjoc.201200690
66. [66]
  R. Li, S. Jiang, H. Zheng, et al., Green Synth. Catal. 3 (2022) 95–101. doi: 10.1016/j.gresc.2021.11.006
67. [67]
  Z. Huang, J. Tang, X. Jiang, Chin. Chem. Lett. 33 (2022) 4842–4845. doi: 10.1016/j.cclet.2022.01.080
68. [68]
  X. Zhu, Y. Huang, X. Xu, F. Qing, Chin. Chem. Lett. 33 (2022) 817–820. doi: 10.1016/j.cclet.2021.07.030
69. [69]
  C. Guo, L. Su, D. Yang, B. Wang, J. Qu, Chin. Chem. Lett. 33 (2022) 217–220. doi: 10.1016/j.cclet.2021.06.070
70. [70]
  Z, Bai, F. Song, H. Wang, et al., CCS Chem. 4 (2022) 2258–2266. doi: 10.31635/ccschem.021.202101056
71. [71]
  G. Wang, J. Yin, J. Li, et al., CCS Chem. 3 (2021) 308–316. doi: 10.31635/ccschem.021.202000712
72. [72]
  L. Chen, P. Ren, B.P. Carrow, J. Am. Chem. Soc. 138 (2016) 6392–6395. doi: 10.1021/jacs.6b03215
73. [73]
  R.B. Bedford, E. Carter, P.M. Cogswell, et al., Angew. Chem. Int. Ed. 52 (2013) 1285-1288. doi: 10.1002/anie.201207868
1. [1]
  Jia-Cheng Hou , Hong-Tao Ji , Yu-Han Lu , Jia-Sheng Wang , Yao-Dan Xu , Yan-Yan Zeng , Wei-Min He . Sustainable and practical semi-heterogeneous photosynthesis of 5-amino-1,2,4-thiadiazoles over WS₂/TEMPO. Chinese Chemical Letters, 2024, 35(8): 109514-. doi: 10.1016/j.cclet.2024.109514
2. [2]
  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
3. [3]
  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
4. [4]
  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
5. [5]
  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
6. [6]
  Pengcheng Su , Shizheng Chen , Zhihong Yang , Ningning Zhong , Chenzi Jiang , Wanbin Li . Vapor-phase postsynthetic amination of hypercrosslinked polymers for efficient iodine capture. Chinese Chemical Letters, 2024, 35(9): 109357-. doi: 10.1016/j.cclet.2023.109357
7. [7]
  Peiwen Liu , Fang Zhao , Jing Zhang , Yunpeng Bai , Jinxing Ye , Bo Bao , Xinggui Zhou , Li Zhang , Changlu Zhou , Xinhai Yu , Peng Zuo , Jianye Xia , Lian Cen , Yangyang Yang , Guoyue Shi , Lin Xu , Weiping Zhu , Yufang Xu , Xuhong Qian . Micro/nano flow chemistry by Beyond Limits Manufacturing. Chinese Chemical Letters, 2024, 35(5): 109020-. doi: 10.1016/j.cclet.2023.109020
8. [8]
  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
9. [9]
  Zhongsen Wang , Lijun Qiu , Yunhua Huang , Meng Zhang , Xi Cai , Fanyu Wang , Yang Lin , Yanbiao Shi , Xiao Liu . Alcohothermal synthesis of sulfidated zero-valent iron for enhanced Cr(Ⅵ) removal. Chinese Chemical Letters, 2024, 35(7): 109195-. doi: 10.1016/j.cclet.2023.109195
10. [10]
  Xianzheng Zhang , Yana Chen , Zhiyong Ye , Huilin Hu , Ling Lei , Feng You , Junlong Yao , Huan Yang , Xueliang Jiang . Magnetic field-assisted microbial corrosion construction iron sulfides incorporated nickel-iron hydroxide towards efficient oxygen evolution. Chinese Journal of Structural Chemistry, 2024, 43(1): 100200-100200. doi: 10.1016/j.cjsc.2023.100200
11. [11]
  Yingxiao Zong , Yangfei Wei , Xiaoqing Liu , Junke Wang , Huanfang Guo , Junli Wang , Zhuangzhi Shi , Tao Tu , Cheng Yang , Chongyang Wang , Leyong Wang . The 4^th CCL Organic Chemistry Forum held in Zhangye. Chinese Chemical Letters, 2024, 35(8): 109743-. doi: 10.1016/j.cclet.2024.109743
12. [12]
  Haiying Lu , Weijie Li . The electrolyte solvation and interfacial chemistry for anode-free sodium metal batteries. Chinese Journal of Structural Chemistry, 2024, 43(11): 100334-100334. doi: 10.1016/j.cjsc.2024.100334
13. [13]
  Xiumei LI , Yanju HUANG , Bo LIU , Yaru PAN . Syntheses, crystal structures, and quantum chemistry calculation of two Ni(Ⅱ) coordination polymers. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 2031-2039. doi: 10.11862/CJIC.20240109
14. [14]
  Wen-Tao Ouyang , Jun Jiang , Yan-Fang Jiang , Ting Li , Yuan-Yuan Liu , Hong-Tao Ji , Li-Juan Ou , Wei-Min He . Sono-photocatalytic amination of quinoxalin-2(1H)-ones with aliphatic amines. Chinese Chemical Letters, 2024, 35(10): 110038-. doi: 10.1016/j.cclet.2024.110038
15. [15]
  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
16. [16]
  Rui Cheng , Tingting Zhang , Xin Huang , Jian Yu . Facile synthesis of high-brightness green-emitting carbon dots with narrow bandwidth towards backlight display. Chinese Chemical Letters, 2024, 35(5): 108763-. doi: 10.1016/j.cclet.2023.108763
17. [17]
  Guiyang Zheng , Xuelian Kang , Haoran Ye , Wei Fan , Christian Sonne , Su Shiung Lam , Rock Keey Liew , Changlei Xia , Yang Shi , Shengbo Ge . Recent advances in functional utilisation of environmentally friendly and recyclable high-performance green biocomposites: A review. Chinese Chemical Letters, 2024, 35(4): 108817-. doi: 10.1016/j.cclet.2023.108817
18. [18]
  Huihui LIU , Baichuan ZHAO , Chuanhui WANG , Zhi WANG , Congyun ZHANG . Green synthesis of MIL-101/Au composite particles and their sensitivity to Raman detection of thiram. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 2021-2030. doi: 10.11862/CJIC.20240059
19. [19]
  Qiongqiong Wan , Yanan Xiao , Guifang Feng , Xin Dong , Wenjing Nie , Ming Gao , Qingtao Meng , Suming Chen . Visible-light-activated aziridination reaction enables simultaneous resolving of C=C bond location and the sn-position isomers in lipids. Chinese Chemical Letters, 2024, 35(4): 108775-. doi: 10.1016/j.cclet.2023.108775
20. [20]
  Xing Tian , Di Wu , Wanheng Wei , Guifu Dai , Zhanxian Li , Benhua Wang , Mingming Yu . A lipid droplets-targetable fluorescent probe for polarity detection in cells of iron death, inflammation and fatty liver tissue. Chinese Chemical Letters, 2024, 35(6): 108912-. doi: 10.1016/j.cclet.2023.108912

Get Citation

PDF

XML

Metrics

PDF Downloads(4)
Abstract views(296)
HTML views(5)

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

Iron/B2pin2 catalytic system enables the generation of alkyl radicals from inert alkyl C-O bonds for amine synthesis

Metrics

通讯作者: 陈斌, bchen63@163.com

Iron/B₂pin₂ catalytic system enables the generation of alkyl radicals from inert alkyl C-O bonds for amine synthesis