Citation: Minghui Zhang, Na Zhang, Qian Zhao, Chao Wang, Alexander Steiner, Jianliang Xiao, Weijun Tang. Cobalt pincer complex-catalyzed highly enantioselective hydrogenation of quinoxalines[J]. Chinese Chemical Letters, ;2025, 36(4): 110081. doi: 10.1016/j.cclet.2024.110081 shu

Cobalt pincer complex-catalyzed highly enantioselective hydrogenation of quinoxalines

Minghui Zhang ^{a, 1} ,
Na Zhang ^{a, 1} ,
Qian Zhao ^a ,
Chao Wang ^a ,
Alexander Steiner ^b ,
Jianliang Xiao ^{b, *,} ,
Weijun Tang ^{a, *,}

a.
Key Laboratory of Applied Surface and Colloid Chemistry of Ministry of Education, and School of Chemistry & Chemical Engineering, Shaanxi Normal University, Xi'an 710062, China
b.
Department of Chemistry, University of Liverpool, Liverpool L69 7ZD, United Kingdom

jxiao@liverpool.ac.uk

tangwj@snnu.edu.cn

Received Date: 18 May 2024
Revised Date: 30 May 2024
Accepted Date: 2 June 2024
Available Online: 3 June 2024

Figures(4)

A cobalt pincer complex bearing both P and C-stereogenic centers has been designed and synthesized, allowing for the development of the first cobalt-catalyzed asymmetric hydrogenation of quinoxalines under relatively mild conditions. Valuable chiral 1,2,3,4-tetrahydroquinoxalines could be obtained with high yields and excellent enantioselectivities (35 examples, up to > 99% ee).
- Cobalt catalysis,
- Pincer PNN ligand,
- Enantioselective hydrogenation,
- Chiral tetrahydroquinoxaline,
- Chiral phosphine
1. [1]
  C.J. Abraham, D.H. Paull, M.T. Scerba, et al., J. Am. Chem. Soc. 128 (2006) 13370–13371. doi: 10.1021/ja065754d
2. [2]
  C.T. Eary, Z.S. Jones, R.D. Groneberg, et al., Bioorg. Med. Chem. Lett. 17 (2007) 2608–2613. doi: 10.1016/j.bmcl.2007.01.112
3. [3]
  R.P. Law, S.J. Atkinson, P. Bamborough, et al., J. Med. Chem. 61 (2018) 4317–4334. doi: 10.1021/acs.jmedchem.7b01666
4. [4]
  J.A. Sikorski, J. Med. Chem. 49 (2006) 1–22. doi: 10.1021/jm058224l
5. [5]
  K. Torisu, K. Kobayashi, M. Iwahashi, et al., Bioorg. Med. Chem. 12 (2004) 5361–5378. doi: 10.1016/j.bmc.2004.07.048
6. [6]
  J.E. Wilson, R. Kurukulasuriya, M. Reibarkh, et al., ACS Med. Chem. Lett. 7 (2016) 261–265. doi: 10.1021/acsmedchemlett.5b00404
7. [7]
  A.K. Sahoo, A. Bhattacharyya, Curr. Org. Chem. 28 (2024) 161–175. doi: 10.2174/0113852728285439240109071659
8. [8]
  D.J. Ager, A.H.M. de Vries, J.G. de Vries, Chem. Soc. Rev. 41 (2012) 3340–3380. doi: 10.1039/c2cs15312b
9. [9]
  A.N. Kim, B.M. Stoltz, ACS Catal. 10 (2020) 13834–13851. doi: 10.1021/acscatal.0c03958
10. [10]
  C.S.G. Seo, R.H. Morris, Organometallics 38 (2019) 47–65. doi: 10.1021/acs.organomet.8b00774
11. [11]
  D.S. Wang, Q.A. Chen, S.M. Lu, et al., Chem. Rev. 112 (2012) 2557–2590. doi: 10.1021/cr200328h
12. [12]
  S. Murata, T. Sugimoto, S. Matsuura, Heterocycles 26 (1987) 763–766. doi: 10.3987/R-1987-03-0763
13. [13]
  C. Bianchini, P. Barbaro, G. Scapacci, et al., Organometallics 17 (1998) 3308–3310. doi: 10.1021/om980219a
14. [14]
  H. Brunner, S. Rosenboem, Monatsh. Chem. 131 (2000) 1371–1382. doi: 10.1007/s007060070017
15. [15]
  J.P. Henschke, M.J. Burk, C.G. Malan, et al., Adv. Synth. Catal. 345 (2003) 300–307. doi: 10.1002/adsc.200390025
16. [16]
  L. Qiu, F.Y. Kwong, J. Wu, et al., J. Am. Chem. Soc. 128 (2006) 5955–5965. doi: 10.1021/ja0602694
17. [17]
  W. Tang, L. Xu, Q.H. Fan, et al., Angew. Chem. Int. Ed. 48 (2009) 9135–9138. doi: 10.1002/anie.200904518
18. [18]
  D. Cartigny, F. Berhal, T. Nagano, et al., J. Org. Chem. 77 (2012) 4544–4556. doi: 10.1021/jo300455y
19. [19]
  D. Cartigny, T. Nagano, T. Ayad, et al., Adv. Synth. Catal. 352 (2010) 1886–1891. doi: 10.1002/adsc.201000513
20. [20]
  B. Li, G. Zhou, D. Zhang, et al., Org. Lett. 26 (2024) 2097–2102. doi: 10.1021/acs.orglett.4c00409
21. [21]
  Y.B. Lu, C.F. Chen, Y.H. Hu, et al., ChemistrySelect 7 (2022) e202200912. doi: 10.1002/slct.202200912
22. [22]
  N. Mrsic, T. Jerphagnon, A.J. Minnaard, et al., Adv. Synth. Catal. 351 (2009) 2549–2552. doi: 10.1002/adsc.200900522
23. [23]
  S. Sun, P. Nagorny, Chem. Commun. 56 (2020) 8432–8435. doi: 10.1039/d0cc03088k
24. [24]
  A. Xu, C. Li, J. Huang, et al., Chem. Sci. 14 (2023) 9024–9032. doi: 10.1039/d3sc00803g
25. [25]
  N. Arai, Y. Saruwatari, K. Isobe, et al., Adv. Synth. Catal. 355 (2013) 2769–2774. doi: 10.1002/adsc.201300604
26. [26]
  T. Okuma, N. Arai, K. Matsumura, Patent, JP2014051458, 2014.
27. [27]
  J. Qin, F. Chen, Z. Ding, et al., Org. Lett. 13 (2011) 6568–6571. doi: 10.1021/ol2029096
28. [28]
  S. Urban, N. Ortega, F. Glorius, Angew. Chem. Int. Ed. 50 (2011) 3803–3806. doi: 10.1002/anie.201100008
29. [29]
  P. Viereck, G. Hierlmeier, P. Tosatti, et al., J. Am. Chem. Soc. 144 (2022) 11203–11214. doi: 10.1021/jacs.2c02007
30. [30]
  Z. Zhang, H. Du, Angew. Chem. Int. Ed. 54 (2015) 623–626. doi: 10.1002/anie.201409471
31. [31]
  K. Gopalaiah, Chem. Rev. 113 (2013) 3248–3296. doi: 10.1021/cr300236r
32. [32]
  H. Pellissier, H. Clavier, Chem. Rev. 114 (2014) 2775–2823. doi: 10.1021/cr4004055
33. [33]
  Y.Y. Li, S.L. Yu, W.Y. Shen, et al., Acc. Chem. Res. 48 (2015) 2587–2598. doi: 10.1021/acs.accounts.5b00043
34. [34]
  P.J. Chirik, Acc. Chem. Res. 48 (2015) 1687–1695. doi: 10.1021/acs.accounts.5b00134
35. [35]
  W. Ai, R. Zhong, X. Liu, et al., Chem. Rev. 119 (2019) 2876–2953. doi: 10.1021/acs.chemrev.8b00404
36. [36]
  W. Sun, Q. Sun, Acc. Chem. Res. 52 (2019) 2370–2381. doi: 10.1021/acs.accounts.9b00285
37. [37]
  J. Guo, Z. Cheng, J. Chen, et al., Acc. Chem. Res. 54 (2021) 2701–2716. doi: 10.1021/acs.accounts.1c00212
38. [38]
  L.J. Li, Y. He, Y. Yang, et al., CCS Chem. 6 (2023) 537–584.
39. [39]
  J. Han, Y.M. He, Y. Pan, et al., CCS Chem. 5 (2023) 2088–2100. doi: 10.31635/ccschem.023.202302781
40. [40]
  J. Wen, F. Wang, X. Zhang, Chem. Soc. Rev. 50 (2021) 3211–3237. doi: 10.1039/d0cs00082e
41. [41]
  H. Wang, J. Wen, X. Zhang, Chem. Rev. 121 (2021) 7530–7567. doi: 10.1021/acs.chemrev.1c00075
42. [42]
  P. Behera, D.S. Ramakrishna, M.M. Chandrasekhar, et al., Chirality 35 (2023) 477–497. doi: 10.1002/chir.23559
43. [43]
  S. Chakrabortty, B. de Bruin, J.G. de Vries, Angew. Chem. Int. Ed. 63 (2024) e202315773. doi: 10.1002/anie.202315773
44. [44]
  S. Fleischer, S. Zhou, S. Werkmeister, et al., Chem. Eur. J. 19 (2013) 4997–5003. doi: 10.1002/chem.201204236
45. [45]
  C. Li, B. Villa-Marcos, J. Xiao, J. Am. Chem. Soc. 131 (2009) 6967–6969. doi: 10.1021/ja9021683
46. [46]
  W. Tang, S. Johnston, J.A. Iggo, et al., Angew. Chem. Int. Ed. 52 (2013) 1668–1672. doi: 10.1002/anie.201208774
47. [47]
  C. Liu, X. Liu, Q. Liu, Chem 9 (2023) 2585–2600. doi: 10.1016/j.chempr.2023.05.006
48. [48]
  L. Zeng, M. Zhao, B. Lin, et al., Org. Lett. 25 (2023) 6228–6233. doi: 10.1021/acs.orglett.3c02530
49. [49]
  H. Yang, Y. Hu, Y. Zou, et al., JACS Au 3 (2023) 2981–2986. doi: 10.1021/jacsau.3c00524
50. [50]
  T. Chen, Y. Zou, Y. Hu, et al., Angew. Chem. Int. Ed. 62 (2023) e202303488. doi: 10.1002/anie.202303488
51. [51]
  S. Chakrabortty, K. Konieczny, F.J. de Zwart, et al., Angew. Chem. Int. Ed. 62 (2023) e202301329. doi: 10.1002/anie.202301329
52. [52]
  P. Lu, H. Wang, Y. Mao, et al., J. Am. Chem. Soc. 144 (2022) 17359–17364. doi: 10.1021/jacs.2c08525
53. [53]
  D. Timelthaler, C. Topf, Synthesis 54 (2021) 629–642.
54. [54]
  T. Du, B. Wang, C. Wang, et al., Chin. Chem. Lett. 32 (2021) 1241–1244. doi: 10.1016/j.cclet.2020.09.011
55. [55]
  H. Zhong, M. Shevlin, P.J. Chirik, J. Am. Chem. Soc. 142 (2020) 5272–5281. doi: 10.1021/jacs.9b13876
56. [56]
  K. Murugesan, V.G. Chandrashekhar, C. Kreyenschulte, et al., Angew. Chem. Int. Ed. 59 (2020) 17408–17412. doi: 10.1002/anie.202004674
57. [57]
  X. Du, Y. Xiao, J.M. Huang, et al., Nat. Commun. 11 (2020) 3239–3248. doi: 10.1038/s41467-020-17057-z
58. [58]
  Y.N. Duan, X. Du, Z. Cui, et al., J. Am. Chem. Soc. 141 (2019) 20424–20433. doi: 10.1021/jacs.9b11070
59. [59]
  I. Sorribes, L. Liu, A. Domenech-Carbo, et al., ACS Catal. 8 (2018) 4545–4557. doi: 10.1021/acscatal.7b04260
60. [60]
  M.R. Friedfeld, H. Zhong, R.T. Ruck, et al., Science 360 (2018) 888–893. doi: 10.1126/science.aar6117
61. [61]
  M.R. Friedfeld, M. Shevlin, G.W. Margulieux, et al., J. Am. Chem. Soc. 138 (2016) 3314–3324. doi: 10.1021/jacs.5b10148
62. [62]
  J. Chen, C. Chen, C. Ji, et al., Org. Lett. 18 (2016) 1594–1597. doi: 10.1021/acs.orglett.6b00453
63. [63]
  F. Chen, A.E. Surkus, L. He, et al., J. Am. Chem. Soc. 137 (2015) 11718–11724. doi: 10.1021/jacs.5b06496
64. [64]
  M.R. Friedfeld, M. Shevlin, J.M. Hoyt, et al., Science 342 (2013) 1076–1080. doi: 10.1126/science.1243550
65. [65]
  S. Monfette, Z.R. Turner, S.P. Semproni, et al., J. Am. Chem. Soc. 134 (2012) 4561–4564. doi: 10.1021/ja300503k
66. [66]
  L. Zhang, Z. Huang, J. Am. Chem. Soc. 137 (2015) 15600–15603. doi: 10.1021/jacs.5b11366
67. [67]
  J. Guo, B. Cheng, X. Shen, et al., J. Am. Chem. Soc. 139 (2017) 15316–15319. doi: 10.1021/jacs.7b09832
68. [68]
  J. Wang, X. Shen, X. Chen, et al., J. Am. Chem. Soc. 145 (2023) 24958–24964.
69. [69]
  Q. Dai, W. Li, Z. Li, et al., J. Am. Chem. Soc. 141 (2019) 20556–20564. doi: 10.1021/jacs.9b11938
70. [70]
  T. Imamoto, H. Tsuruta, Chem. Lett. 25 (2006) 707–708.
71. [71]
  Y. Wada, T. Imamoto, H. Tsuruta, et al., Adv. Synth. Catal. 346 (2004) 777–788. doi: 10.1002/adsc.200404043
72. [72]
  T. Imamoto, T. Oshiki, T. Onozawa, et al., J. Am. Chem. Soc. 112 (1990) 5244–5252. doi: 10.1021/ja00169a036
73. [73]
  S. Li, W. Meng, H. Du, Org. Lett. 19 (2017) 2604–2606. doi: 10.1021/acs.orglett.7b00935
74. [74]
  G. Chang, M.T. Didiuk, J.I. Finneman, et al., Patent, WO2004085401, 2004.
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