Citation: Jieshuai Xiao, Yuan Zheng, Yue Zhao, Zhuangzhi Shi, Minyan Wang. Asymmetric Nozaki-Hiyama-Kishi (NHK)-type reaction of isatins with aromatic iodides by cobalt catalysis[J]. Chinese Chemical Letters, ;2025, 36(5): 110243. doi: 10.1016/j.cclet.2024.110243 shu

Asymmetric Nozaki-Hiyama-Kishi (NHK)-type reaction of isatins with aromatic iodides by cobalt catalysis

State Key Laboratory of Coordination Chemistry, Chemistry and Biomedicine Innovation Center (ChemBIC), School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, China

wangmy@nju.edu.cn

Received Date: 1 March 2024
Revised Date: 3 July 2024
Accepted Date: 11 July 2024
Available Online: 14 July 2024

Figures(6)

The asymmetric addition of aromatic organometallic compounds to the carbonyl group (C-3) of isatins, catalyzed by transition metals, has emerged as a remarkably efficient method for the synthesis of chiral 3-hydroxyoxindoles. Here, an exceptionally enantioselective approach was developed for the first time to achieve a catalytic NHK reaction of isatins with aromatic halides (both aryl and heteroaryl). Utilizing chiral cobalt complexes as catalysts, and the presence of a diboron reagent B₂nep₂ as both a reducing agent and determinant in enantiocontrol, has resulted in the triumphantly achieved synthesis of enantioenriched products. Compared to reported strategies, this approach exhibits remarkable compatibility with substrates bearing sensitive functional groups, such as halides and borate esters, while also eliminating the need for organometallic reagents as required in previous strategies. Through experimental investigations, the presence of aryl-cobalt species during the addition process was confirmed, rather than in-situ generation of an arylboron reagent. Furthermore, the successful attainment of the R absolute configuration through aryl addition was demonstrated.
- Enantioselectivity,
- Isatin,
- Cobalt,
- Addition,
- DFT calculations
1. [1]
  J. Bergman, J.O. Lindstrom, U. Tilstam, Tetrahedron 41 (1985) 2879–2881. doi: 10.1016/S0040-4020(01)96609-8
2. [2]
  I. Chiyanzu, E. Hansell, J. Gut, et al., Bioorg. Med. Chem. Lett. 13 (2003) 3527–3530. doi: 10.1016/S0960-894X(03)00756-X
3. [3]
  C.V. Galliford, K.A. Scheidt, Angew. Chem. Int. Ed. 46 (2007) 8748–8758. doi: 10.1002/anie.200701342
4. [4]
  B. Tan, N.R. Candeias, C.F. Barbas Ⅲ, Nat. Chem. 3 (2011) 473–477. doi: 10.1038/nchem.1039
5. [5]
  L. Hong, R. Wang, Adv. Synth. Catal. 355 (2013) 1023–1052. doi: 10.1002/adsc.201200808
6. [6]
  B.M. Trost, D.A. Bringley, T. Zhang, N. Cramer, J. Am. Chem. Soc. 135 (2013) 16720–16735. doi: 10.1021/ja409013m
7. [7]
  Y. Zhao, L. Liu, W. Sun, et al., J. Am. Chem. Soc. 135 (2013) 7223–7234. doi: 10.1021/ja3125417
8. [8]
  B. Yu, D. Yu, H. Liu, Eur. J. Med. Chem. 97 (2015) 673–698. doi: 10.1016/j.ejmech.2014.06.056
9. [9]
  B. Yu, Z. Yu, P.P. Qi, D.Q. Yu, H.M. Liu, Eur. J. Med. Chem. 95 (2015) 35–40. doi: 10.1016/j.ejmech.2015.03.020
10. [10]
  G.S. Singh, Z.Y. Desta, Chem. Rev. 112 (2012) 6104–6155. doi: 10.1021/cr300135y
11. [11]
  R. Zeng, G. Dong, J. Am. Chem. Soc. 137 (2015) 1408–1411. doi: 10.1021/ja512306a
12. [12]
  X.C. Qiao, S.F. Zhu, Q.L. Zhou, Tetrahedron: Asymmetry 20 (2009) 1254–1261. doi: 10.1016/j.tetasy.2009.04.012
13. [13]
  K. Zheng, C. Yin, X. Liu, et al., Angew. Chem. Int. Ed. 50 (2011) 2573–2577. doi: 10.1002/anie.201007145
14. [14]
  S. Periyaraja, A.B. Mandal, P. Shanmugam, Org. Lett. 13 (2011) 4980–4983. doi: 10.1021/ol2022164
15. [15]
  J. Guang, Q. Guo, J.C. Zhao, Org. Lett. 14 (2012) 3174–3177. doi: 10.1021/ol301270w
16. [16]
  G.W. Wang, A.X. Zhou, J.J. Wang, R.B. Hu, S.D. Yang, Org. Lett. 14 (2012) 2218–2221. doi: 10.1080/00103624.2012.701684
17. [17]
  G.W. Wang, A.X. Zhou, J.J. Wang, R.B. Hu, S.D. Yang, Org. Lett. 15 (2013) 5270–5273. doi: 10.1021/ol402494e
18. [18]
  D. Cheng, Y. Ishihara, B. Tan, C.F. Barbas, ACS Catal. 4 (2014) 743–762. doi: 10.1021/cs401172r
19. [19]
  Y. Kuang, Y. Lu, Y. Tang, et al., Org. Lett. 16 (2014) 4244–4247. doi: 10.1021/ol501941n
20. [20]
  K. Pratap, A. Kumar, Org. Lett. 20 (2018) 7451–7454. doi: 10.1021/acs.orglett.8b03196
21. [21]
  Y. Liu, Y.T. Xia, S.H. Cui, Y.G. Ji, L. Wu, Adv. Synth. Catal. 362 (2020) 2632–2636. doi: 10.1002/adsc.202000266
22. [22]
  J. Khan, A. Tyagi, N. Yadav, R. Mahato, C.K. Hazra, J. Org. Chem. 86 (2021) 17833–17847. doi: 10.1021/acs.joc.1c02058
23. [23]
  B. Yu, H. Xing, D.Q. Yu, H.M. Liu, Beilstein J. Org. Chem. 12 (2016) 1000–1039. doi: 10.3762/bjoc.12.98
24. [24]
  S. Um, D.H. Bach, B. Shin, et al., Org. Lett. 18 (2016) 5792–5795. doi: 10.1021/acs.orglett.6b02555
25. [25]
  T. Tokunaga, W.E. Hume, T. Umezome, et al., J. Med. Chem. 44 (2001) 4641–4649. doi: 10.1021/jm0103763
26. [26]
  K.C. Nicolaou, M. Bella, D.Y.K. Chen, et al., Angew. Chem. Int. Ed. 41 (2002) 3495–3499. doi: 10.1002/1521-3773(20020916)41:18<3495::AID-ANIE3495>3.0.CO;2-7
27. [27]
  A.W.G. Burgett, Q. Li, Q. Wei, P.G. Harran, Angew. Chem. Int. Ed. 42 (2003) 4961–4966. doi: 10.1002/anie.200352577
28. [28]
  K.C. Nicolaou, M. Bella, D.Y.K. Chen, et al., J. Am. Chem. Soc. 126 (2004) 12888–12896. doi: 10.1021/ja040092i
29. [29]
  R.R. Knowles, J. Carpenter, S.B. Blakey, et al., Chem. Sci. 2 (2011) 308–311. doi: 10.1039/C0SC00577K
30. [30]
  R. Shintani, M. Inoue, T. Hayashi, Angew. Chem. Int. Ed. 45 (2006) 3353–3356. doi: 10.1002/anie.200600392
31. [31]
  S. Lu, S.B. Poh, W.Y. Siau, Y. Zhao, Angew. Chem. Int. Ed. 52 (2013) 1731–1734. doi: 10.1002/anie.201209043
32. [32]
  H. Lai, Z. Huang, Q. Wu, Y. Qin, J. Org. Chem. 74 (2009) 283–288. doi: 10.1021/jo802036m
33. [33]
  R. Shintani, K. Takatsu, T. Hayashi, Chem. Commun. 46 (2010) 6822–6824. doi: 10.1039/c0cc01635g
34. [34]
  J. Zhang, J. Chen, J. Ding, M. Liu, H. Wu, Tetrahedron 67 (2011) 9347–9351. doi: 10.1016/j.tet.2011.09.135
35. [35]
  Z. Liu, P. Gu, M. Shi, P. McDowell, G. Li, Org. Lett. 13 (2011) 2314–2317. doi: 10.1021/ol200566s
36. [36]
  Y. Yamamoto, M. Yohda, T. Shirai, H. Ito, N. Miyaura, Chem. Asian J. 7 (2012) 2446–2449. doi: 10.1002/asia.201200481
37. [37]
  J. Gui, G. Chen, P. Cao, J. Liao, Tetrahedron Asymmetry 23 (2012) 554–563. doi: 10.1016/j.tetasy.2012.04.013
38. [38]
  Y. Zhuang, Y. He, Z. Zhou, et al., J. Org. Chem. 80 (2015) 6968–6975. doi: 10.1021/acs.joc.5b00595
39. [39]
  J. Totobenazara, P. Bacalhau, A.A.S. Juan, et al., ChemistrySelect 1 (2016) 3580–3588. doi: 10.1002/slct.201600932
40. [40]
  C.S. Marques, A.J. Burke, ChemCatChem 8 (2016) 3518–3526. doi: 10.1002/cctc.201600901
41. [41]
  Y.Y. Zhang, H. Chen, X. Jiang, et al., Tetrahedron 74 (2018) 2245–2250. doi: 10.1016/j.tet.2018.03.039
42. [42]
  W. Guo, S. Zhan, H. Yang, Z. Gu, Org. Lett. 25 (2023) 3281–3286. doi: 10.1021/acs.orglett.3c01028
43. [43]
  D. Tomita, K. Yamatsugu, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 131 (2009) 6946–6948. doi: 10.1021/ja901995a
44. [44]
  X.A.F. Cook, A. de Gombert, J. McKnight, L.R.E. Pantaine, M.C. Willis, Angew. Chem. Int. Ed. 60 (2021) 11068–11091. doi: 10.1002/anie.202010631
45. [45]
  Y. Okude, S. Hirano, T. Hiyama, H. Nozaki, J. Am. Chem. Soc. 99 (1977) 3179–3181. doi: 10.1021/ja00451a061
46. [46]
  H. Jin, J. Uenishi, W.J. Christ, Y. Kishi, J. Am. Chem. Soc. 108 (1986) 5644–5646. doi: 10.1021/ja00278a057
47. [47]
  D.A. Everson, D.J. Weix, J. Org. Chem. 79 (2014) 4793–4798. doi: 10.1021/jo500507s
48. [48]
  C.E.I. Knappke, S. Grupe, D. Gartner, et al., Chem. Eur. J. 20 (2014) 6828–6842. doi: 10.1002/chem.201402302
49. [49]
  T. Moragas, A. Correa, R. Martin, Chem. Eur. J. 20 (2014) 8242–8258. doi: 10.1002/chem.201402509
50. [50]
  D.J. Weix, Acc. Chem. Res. 48 (2015) 1767–1775. doi: 10.1021/acs.accounts.5b00057
51. [51]
  J. Gu, X. Wang, W. Xue, H. Gong, Org. Chem. Front. 2 (2015) 1411–1421. doi: 10.1039/C5QO00224A
52. [52]
  K.E. Poremba, S.E. Dibrell, S.E. Reisman, ACS Catal. 10 (2020) 8237–8246. doi: 10.1021/acscatal.0c01842
53. [53]
  W. Xue, X. Jia, X. Wang, et al., Chem. Soc. Rev. 50 (2021) 4162–4184. doi: 10.1039/d0cs01107j
54. [54]
  A. Duan, F. Xiao, Y. Lan, L. Niu, Chem. Soc. Rev. 51 (2022) 9986–10015. doi: 10.1039/d2cs00371f
55. [55]
  X. Pang, P.F. Su, X.Z. Shu, Acc. Chem. Res. 55 (2022) 2491–2509. doi: 10.1021/acs.accounts.2c00381
56. [56]
  L. Xi, L. Du, Z. Shi, Chin. Chem. Lett. 33 (2022) 4287–4292. doi: 10.1016/j.cclet.2022.01.077
57. [57]
  Y. Dai, F. Wang, S. Zhu, L. Chu, Chin. Chem. Lett. 33 (2022) 4074–4078. doi: 10.1016/j.cclet.2021.12.050
58. [58]
  A. Nasim, G.T. Thomas, J.S. Ovens, et al., Org. Lett. 24 (2022) 7232–7236. doi: 10.1021/acs.orglett.2c03042
59. [59]
  H. Chang, M. Jeganmohan, C. Cheng, Chem. Eur. J. 13 (2007) 4356–4363. doi: 10.1002/chem.200601880
60. [60]
  H. Tao Jia, Q.S. Tian, J.N. Xiang, G.Z. Zhang, Chin. Chem. Lett. 28 (2017) 1182–1184. doi: 10.1016/j.cclet.2017.03.016
61. [61]
  Z. Zhu, J. Xiao, M. Li, Z. Shi, Angew. Chem. Int. Ed. 61 (2022) e202201370. doi: 10.1002/anie.202201370
62. [62]
  S. Zhang, S. Perveen, Y. Ouyang, et al., Angew. Chem. Int. Ed. 61 (2022) e202117843. doi: 10.1002/anie.202117843
63. [63]
  X. Jiang, H. Jiang, Q. Yang, et al., J. Am. Chem. Soc. 144 (2022) 8347–8354. doi: 10.1021/jacs.2c02481
64. [64]
  L. Zhang, M. Zhao, M. Pu, et al., J. Am. Chem. Soc. 144 (2022) 20249–20257. doi: 10.1021/jacs.2c05678
65. [65]
  J. Xiao, M. Wang, X. Yin, et al., Angew. Chem. Int. Ed. 62 (2023) e202300743. doi: 10.1002/anie.202300743
66. [66]
  H. Jiang, X.K. He, X. Jiang, et al., J. Am. Chem. Soc. 145 (2023) 6944–6952. doi: 10.1021/jacs.3c00462
67. [67]
  L. Zhang, X. Wang, M. Pu, et al., J. Am. Chem. Soc. 145 (2023) 8498–8509. doi: 10.1021/jacs.3c00548
68. [68]
  T. Liang, Y. Wu, J. Sun, et al., Chin. J. Chem. 41 (2023) 3253–3260. doi: 10.1002/cjoc.202300398
69. [69]
  L.J. Li, Y. He, Y. Yang, et al., CCS Chem. 6 (2024) 537–584. doi: 10.31635/ccschem.023.202303412
70. [70]
  C.H. Wei, S. Mannathan, C.H. Cheng, J. Am. Chem. Soc. 133 (2011) 6942–6944. doi: 10.1021/ja201827j
71. [71]
  T. Sawano, A. Ashouri, T. Nishimura, T. Hayashi, J. Am. Chem. Soc. 134 (2012) 18936–18939. doi: 10.1021/ja309756k
72. [72]
  K. Duvvuri, K.R. Dewese, M.M. Parsutkar, et al., J. Am. Chem. Soc. 141 (2019) 7365–7375. doi: 10.1021/jacs.8b13812
73. [73]
  Y.L. Li, S.Q. Zhang, J. Chen, J.B. Xia, J. Am. Chem. Soc. 143 (2021) 7306–7313. doi: 10.1021/jacs.1c03527
74. [74]
  K. Cui, Y.L. Li, G. Li, J.B. Xia, J. Am. Chem. Soc. 144 (2022) 23001–23009. doi: 10.1021/jacs.2c10021
75. [75]
  P. Yang, Q. Wang, B.H. Cui, et al., J. Am. Chem. Soc. 144 (2022) 1087–1093. doi: 10.1021/jacs.1c11092
76. [76]
  X. Jiang, W. Xiong, S. Deng, et al., Nat. Catal. 5 (2022) 788–797. doi: 10.1038/s41929-022-00831-1
77. [77]
  A. Li, X. Song, Q. Ren, et al., Angew. Chem. Int. Ed. 62 (2023) e202301091. doi: 10.1002/anie.202301091
78. [78]
  W. Xiong, X. Jiang, W.C. Wang, et al., J. Am. Chem. Soc. 145 (2023) 7983–7991. doi: 10.1021/jacs.2c13538
79. [79]
  Z.L. Zhang, Z. Li, Y.T. Xu, et al., Angew. Chem. Int. Ed. 62 (2023) e202306381. doi: 10.1002/anie.202306381
80. [80]
  W. Huang, J. Bai, Y. Guo, Q, Chong, F. Meng, Angew. Chem. Int. Ed. 62 (2023) e202219257. doi: 10.1002/anie.202219257
81. [81]
  Z. Liang, L. Wang, Y. Wang, et al., J. Am. Chem. Soc. 145 (2023) 3588–3598. doi: 10.1021/jacs.2c12475
82. [82]
  H. Wang, X. Jie, Q. Chong, F. Meng, Nat. Commun. 15 (2024) 3427. doi: 10.1038/s41467-024-47719-1
83. [83]
  L. Wang, Y. Tong, X. Lu, Y. Fu, Chin. Chem. Lett. 35 (2024) 109283. doi: 10.1016/j.cclet.2023.109283
84. [84]
  M. Aresta, M. Rossi, A. Sacco, Inorg. Chim. Acta 3 (1969) 227–231. doi: 10.1016/S0020-1693(00)92484-8
85. [85]
  K. Heinze, G. Huttner, L. Zsolnai, P. Schober, Inorg. Chem. 36 (1997) 5457–5469. doi: 10.1021/ic9705352
86. [86]
  M. Gray, M.T. Hines, M.M. Parsutkar, et al., ACS Catal. 10 (2020) 4337–4348. doi: 10.1021/acscatal.9b05455
87. [87]
  L. Wang, L. Wang, M. Li, Q. Chong, F. Meng, J. Am. Chem. Soc. 143 (2021) 12755–12765. doi: 10.1021/jacs.1c05690
88. [88]
  M.R. Friedfeld, H. Zhong, R.T. Ruck, M. Shevlin, P.J. Chirik, Science 360 (2018) 888–893. doi: 10.1126/science.aar6117
89. [89]
  H. Zhong, M.R. Friedfeld, P.J. Chirik, Angew. Chem. Int. Ed. 58 (2019) 9194–9198. doi: 10.1002/anie.201903766
90. [90]
  D. Guillaneux, S. Zhao, O. Samuel, D. Rainford, H.B. Kagan, J. Am. Chem. Soc. 116 (1994) 9430–9439. doi: 10.1021/ja00100a004
91. [91]
  C. Girard, H.B. Kagan, Angew. Chem. Int. Ed. 37 (1998) 2922–2959. doi: 10.1002/(SICI)1521-3773(19981116)37:21<2922::AID-ANIE2922>3.0.CO;2-1
92. [92]
  X. Lu, Y. Wang, B. Zhang, et al., J. Am. Chem. Soc. 139 (2017) 12632–12637. doi: 10.1021/jacs.7b06469
93. [93]
  J. Sheng, H.Q. Ni, S.X. Ni, et al., Angew. Chem. Int. Ed. 60 (2021) 15020–15027. doi: 10.1002/anie.202102481
94. [94]
  T. Lu, Q. Chen, J. Comput. Chem. 43 (2022) 539–555. doi: 10.1002/jcc.26812
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  Chuan-Zhi Ni , Ruo-Ming Li , Fang-Qi Zhang , Qu-Ao-Wei Li , Yuan-Yuan Zhu , Jie Zeng , Shuang-Xi Gu . A chiral fluorescent probe for molecular recognition of basic amino acids in solutions and cells. Chinese Chemical Letters, 2024, 35(10): 109862-. doi: 10.1016/j.cclet.2024.109862
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  Yuanjin Chen , Xianghui Shi , Dajiang Huang , Junnian Wei , Zhenfeng Xi . Synthesis and reactivity of cobalt dinitrogen complex supported by nonsymmetrical pincer ligand. Chinese Chemical Letters, 2024, 35(7): 109292-. doi: 10.1016/j.cclet.2023.109292
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