Citation: Wenju Chang, Yajun Wang, Yu Chen, Jiawei Ma, Yong Liang. Control of meta-selectivity in the Ir-catalyzed aromatic C-H borylation directed by hydrogen bond interaction: A combined computational and experimental study[J]. Chinese Chemical Letters, ;2023, 34(5): 107879. doi: 10.1016/j.cclet.2022.107879 shu

Control of meta-selectivity in the Ir-catalyzed aromatic C-H borylation directed by hydrogen bond interaction: A combined computational and experimental study

State Key Laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials, Chemistry and Biomedicine Innovation Center, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, China

yongliang@nju.edu.cn

Received Date: 5 July 2022
Revised Date: 28 September 2022
Accepted Date: 2 October 2022
Available Online: 4 October 2022

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The origin of regioselectivity in meta-selective C-H borylation of benzamides directed by hydrogen bond interaction between ligand and substrate is elucidated through combined computational and experimental studies. We discover that a non-directed pathway, in which the urea moiety in ligand recognizes the O atom in Bpin instead of substrate, competes with the directed pathway and erodes the meta-selectivity. The non-directed pathway is sensitive to steric repulsion between Bpin and urea, and thus can be impeded by introducing a bulky substituent into the urea moiety. Accordingly, we optimize the ligand and improve the meta-selectivity in the Ir-catalyzed C-H borylation of some previously reported unsuccessful arenes.
- Meta-C-H borylation,
- Regioselectivity,
- DFT calculation,
- Ligand design,
- Hydrogen bond
1. [1]
  G. Meng, N.Y.S. Lam, E.L. Lucas, et al., J. Am. Chem. Soc. 142 (2020) 10571–10591. doi: 10.1021/jacs.0c04074
2. [2]
  T.W. Lyons, M.S. Sanford, Chem. Rev. 110 (2010) 1147–1169. doi: 10.1021/cr900184e
3. [3]
  R. Bisht, C. Haldar, M.M.M. Hassan, et al., Chem. Soc. Rev. 51 (2022) 5042–5100. doi: 10.1039/d1cs01012c
4. [4]
  V. Snieckus, Chem. Rev. 90 (1990) 879–933. doi: 10.1021/cr00104a001
5. [5]
  S.R. Neufeldt, M.S. Sanford, Acc. Chem. Res. 45 (2012) 936–946. doi: 10.1021/ar300014f
6. [6]
  Z. Chen, B. Wang, J. Zhang, et al., Org. Chem. Front. 2 (2015) 1107–1295. doi: 10.1039/C5QO00004A
7. [7]
  Z.R. Wang, P.P. Xie, Y.Z. Xia, Chin. Chem. Lett. 29 (2018) 47–53. doi: 10.11648/j.ajmsp.20180303.12
8. [8]
  M.T. Mihai, G.R. Genov, R.J. Phipps, Chem. Soc. Rev. 47 (2018) 149–171. doi: 10.1039/C7CS00637C
9. [9]
  U. Dutta, S. Maiti, T. Bhattacharya, D. Maiti, Science 372 (2021) eabd5992. doi: 10.1126/science.abd5992
10. [10]
  J.A. Leitch, C.G. Frost, Chem. Soc. Rev. 46 (2017) 7145–7153. doi: 10.1039/C7CS00496F
11. [11]
  N. Hofmann, L. Ackermann, J. Am. Chem. Soc. 135 (2013) 5877–5884. doi: 10.1021/ja401466y
12. [12]
  C.J. Teskey, A.Y.W. Lui, M.F. Greaney, Angew. Chem. Int. Ed. 54 (2015) 11677–11680. doi: 10.1002/anie.201504390
13. [13]
  C.C. Yuan, L. Zhu, C.P. Chen, et al., Nat. Commun. 9 (2018) 1189–1198. doi: 10.1038/s41467-018-03341-6
14. [14]
  A. Dey, S.K. Sinha, T.K. Achar, D. Maiti, Angew. Chem. Int. Ed. 58 (2019) 10820–10843. doi: 10.1002/anie.201812116
15. [15]
  D. Leow, G. Li, T.S. Mei, J.Q. Yu, Nature 486 (2012) 518–522. doi: 10.1038/nature11158
16. [16]
  R.Y. Tang, G. Li, J.Q. Yu, Nature 507 (2014) 215–220. doi: 10.1038/nature12963
17. [17]
  S. Lee, H. Lee, K.L. Tan, J. Am. Chem. Soc. 135 (2013) 18778–18781. doi: 10.1021/ja4107034
18. [18]
  Y.F. Yang, G.J. Cheng, P. Liu, et al., J. Am. Chem. Soc. 136 (2014) 344–355. doi: 10.1021/ja410485g
19. [19]
  S. Bag, T. Patra, A. Modak, et al., J. Am. Chem. Soc. 137 (2015) 11888–11891. doi: 10.1021/jacs.5b06793
20. [20]
  M. Bera, A. Maji, S.K. Sahoo, D. Maiti, Angew. Chem. Int. Ed. 54 (2015) 8515–8519. doi: 10.1002/anie.201503112
21. [21]
  Z.P. Zhang, K. Tanaka, J.Q. Yu, Nature 543 (2017) 538–542. doi: 10.1038/nature21418
22. [22]
  M. Liu, L.J. Li, J. Zhang, et al., Chin. Chem. Lett. 31 (2020) 1301–1304. doi: 10.1016/j.cclet.2019.09.057
23. [23]
  Y. Kuninobu, H. Ida, M. Nishi, M. Kanai, Nat. Chem. 7 (2015) 712–717. doi: 10.1038/nchem.2322
24. [24]
  R. Bisht, B. Chattopadhyay, J. Am. Chem. Soc. 138 (2016) 84–87. doi: 10.1021/jacs.5b11683
25. [25]
  H.J. Davis, M.T. Mihai, R.J. Phipps, J. Am. Chem. Soc. 138 (2016) 12759–12762. doi: 10.1021/jacs.6b08164
26. [26]
  H.J. Davis, G.R. Genov, R.J. Phipps, Angew. Chem. Int. Ed. 56 (2017) 13351–13355. doi: 10.1002/anie.201708967
27. [27]
  M.E. Hoque, R. Bisht, C. Haldar, B. Chattopadhyay, J. Am. Chem. Soc. 139 (2017) 7745–7748. doi: 10.1021/jacs.7b04490
28. [28]
  L. Yang, K. Semba, Y. Nakao, Angew. Chem. Int. Ed. 56 (2017) 4853–4857. doi: 10.1002/anie.201701238
29. [29]
  R. Bisht, M.E. Hoque, B. Chattopadhyay, Angew. Chem. Int. Ed. 57 (2018) 15762–15766. doi: 10.1002/anie.201809929
30. [30]
  L.C. Yang, N. Uemura, Y. Nakao, J. Am. Chem. Soc. 141 (2019) 7972–7979. doi: 10.1021/jacs.9b03138
31. [31]
  G. Liao, Y.J. Wu, B.F. Shi, Acta Chim. Sin. 78 (2020) 289–298. doi: 10.6023/a20020027
32. [32]
  J. Trouvé, P. Zardi, S. Al-Shehimy, T. Roisnel, R. Gramage-Doria, Angew. Chem. Int. Ed. 60 (2021) 18006–18013. doi: 10.1002/anie.202101997
33. [33]
  S. Lu, T. Zheng, J. Ma, et al., Angew. Chem. Int. Ed. 61 (2022) e202201285.
34. [34]
  X.C. Wang, W. Gong, L.Z. Fang, et al., Nature 519 (2015) 334–338. doi: 10.1038/nature14214
35. [35]
  H. Shi, A.N. Herron, Y. Shao, et al., Nature 558 (2018) 581–585. doi: 10.1038/s41586-018-0220-1
36. [36]
  J.C. Wang, G.B. Dong, Chem. Rev. 119 (2019) 7478–7528. doi: 10.1021/acs.chemrev.9b00079
37. [37]
  J. Cornella, M. Righi, I. Larrosa, Angew. Chem. Int. Ed. 50 (2011) 9429–9432. doi: 10.1002/anie.201103720
38. [38]
  R.J. Phipps, M.J. Gaunt, Science 323 (2009) 1593–1597. doi: 10.1126/science.1169975
39. [39]
  Y. Nakao, Y. Yamada, N. Kashihara, T. Hiyama, J. Am. Chem. Soc. 132 (2010) 13666–13668. doi: 10.1021/ja106514b
40. [40]
  C.L. Ciana, R.J. Phipps, J.R. Brandt, et al., Angew. Chem. Int. Ed. 50 (2011) 458–462. doi: 10.1002/anie.201004703
41. [41]
  N.A. Romero, K.A. Margrey, N.E. Tay, D.A. Nicewicz, Science 349 (2015) 1326–1330. doi: 10.1126/science.aac9895
42. [42]
  Y. Saito, Y. Segawa, K. Itami, J. Am. Chem. Soc. 137 (2015) 5193–5198. doi: 10.1021/jacs.5b02052
43. [43]
  F. Berger, M.B. Plutschack, J. Riegger, et al., Nature 567 (2019) 223–228. doi: 10.1038/s41586-019-0982-0
44. [44]
  C. Haldar, M.E. Hogue, R. Bisht, B. Chattopadhyay, Tetrahedron Lett. 59 (2018) 1269–1277. doi: 10.1016/j.tetlet.2018.01.098
45. [45]
  Y. Kuroda, Y. Nakao, Chem. Lett. 48 (2019) 1092–1100. doi: 10.1246/cl.190372
46. [46]
  X.L. Zou, S.M. Xu, Chin. J. Org. Chem. 41 (2021) 2610–2620. doi: 10.6023/cjoc202103020
47. [47]
  S. Pandit, S. Maiti, D. Maiti, Org. Chem. Front. 8 (2021) 4349–4358. doi: 10.1039/d1qo00452b
48. [48]
  I.A.I. Mkhalid, J.H. Barnard, T.B. Marder, et al., Chem. Rev. 110 (2010) 890–931. doi: 10.1021/cr900206p
49. [49]
  J.W.B. Fyfe, A.J.B. Watson, Chem 3 (2017) 31–55. doi: 10.1016/j.chempr.2017.05.008
50. [50]
  J. Hu, M. Ferger, Z. Shi, T.B. Marder, Chem. Soc. Rev. 50 (2021) 13129–13188. doi: 10.1039/d0cs00843e
51. [51]
  J. Lv, B. Zhao, Y. Han, et al., Chin. Chem. Lett. 32 (2021) 691–694. doi: 10.1016/j.cclet.2020.06.028
52. [52]
  H. Tamura, H. Yamazaki, H. Sato, S. Sakaki, J. Am. Chem. Soc. 125 (2003) 16114–16126. doi: 10.1021/ja0302937
53. [53]
  T.M. Boller, J.M. Murphy, M. Hapke, et al., J. Am. Chem. Soc. 127 (2005) 14263–14278. doi: 10.1021/ja053433g
54. [54]
  A.G. Green, P. Liu, C.A. Merlic, K.N. Houk, J. Am. Chem. Soc. 136 (2014) 4575–4583. doi: 10.1021/ja411699u
55. [55]
  X. Zou, H. Zhao, Y. Li, et al., J. Am. Chem. Soc. 141 (2019) 5334–5342. doi: 10.1021/jacs.8b13756
56. [56]
  A. Unnikrishnan, R.B. Sunoj, Chem. Sci. 10 (2019) 3826–3835. doi: 10.1039/C8SC05335A
57. [57]
  G. Pupo, V. Gouverneur, J. Am. Chem. Soc. 144 (2022) 5200–5213. doi: 10.1021/jacs.2c00190
58. [58]
  N. Oka, T. Yamada, H. Sajiki, et al., Org. Lett. 24 (2022) 3510–3514. doi: 10.1021/acs.orglett.2c01174
59. [59]
  T. Ishiyama, J. Takagi, J.F. Hartwig, N. Miyaura, Angew. Chem. Int. Ed. 41 (2002) 3056–3058. doi: 10.1002/1521-3773(20020816)41:16<3056::AID-ANIE3056>3.0.CO;2-#
60. [60]
  T. Ishiyama, J. Takagi, K. Ishida, et al., J. Am. Chem. Soc. 124 (2002) 390–391. doi: 10.1021/ja0173019
61. [61]
  W. Chang, Y. Chen, S. Lu, et al., Chem 8 (2022) 1775–1788. doi: 10.1016/j.chempr.2022.04.025
62. [62]
  Y. Wang, W. Chang, S. Qin, et al., Angew. Chem. Int. Ed. 61 (2022) e202206797.
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