Citation: Dong Wu, Hailiang Pang, Guoyin Yin. 1,1-Regioselective alkenylboration of styrenes enabled by palladium catalysis[J]. Chinese Chemical Letters, ;2023, 34(8): 108087. doi: 10.1016/j.cclet.2022.108087 shu

1,1-Regioselective alkenylboration of styrenes enabled by palladium catalysis

The Institute for Advanced Studies, Wuhan University, Wuhan 430072, China

yinguoyin@whu.edu.cn

Received Date: 3 November 2022
Revised Date: 16 December 2022
Accepted Date: 19 December 2022
Available Online: 21 December 2022

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Despite the 1,2-difunctionalization reactions of styrenes have been well developed, the 1,1-regioselective addition reaction remains challenging. We disclose herein a palladium-catalyzed, highly 1,1-regioselective alkenylboration of styrenes by using alkenyl triflates and a diboron reagent as the coupling partners. A wide scope of styrenes derivatives and alkenyl triflates participate this reaction to provide the corresponding allyl boronates with high regioisomeric ratios. The success of this reaction is ascribed to the application of 1,10-phenanthroline-derivated ligand and the addition of ammonium chloride salt. Moreover, acrylate esters can also selectively afford the 1,1-alkenylboration products under the same reaction conditions.
- Styrenes,
- 1,1-Regioselectivity,
- Chain-walking,
- Palladium catalysis,
- Allyl boronates
1. [1]
  M. Beller, J. Seayad, A. Tillack, H. Jiao, Angew. Chem. Int. Ed. 43 (2004) 3368–3398. doi: 10.1002/anie.200300616
2. [2]
  R.I. McDonald, G. Liu, S.S. Stahl, Chem. Rev. 111 (2011) 2981–3019. doi: 10.1021/cr100371y
3. [3]
  S. Zhu, X. Zhao, H. Li, L. Chu, Chem. Soc. Rev. 50 (2021) 10836–10856. doi: 10.1039/D1CS00399B
4. [4]
  X. Zhang, J. Fang, C. Cai, G. Lu, Chin. Chem. Lett. 32 (2021) 1280–1292. doi: 10.1016/j.cclet.2020.09.058
5. [5]
  Y.F. Zheng, J. Yu, G.B. Yan, X. Li, S. Luo, Chin. Chem. Lett. 22 (2011) 1195–1198.
6. [6]
  J. Derosa, O. Apolinar, T. Kang, V.T. Tran, K.M. Engle, Chem. Sci. 11 (2020) 4287–4296. doi: 10.1039/C9SC06006E
7. [7]
  Z.L. Li, G.C. Fang, Q.S. Gu, X.Y. Liu, Chem. Soc. Rev. 49 (2020) 32–48. doi: 10.1039/C9CS00681H
8. [8]
  X. Fu, W. Zhao, Chin. J. Org. Chem. 39 (2019) 625–647. doi: 10.6023/cjoc201808031
9. [9]
  Y.C. Luo, C. Xu, X. Zhang, Chin. J. Chem. 38 (2020) 1371–1394. doi: 10.1002/cjoc.202000224
10. [10]
  J.S. Zhang, L. Liu, T. Chen, L.B. Han, Chem. Asian J. 13 (2018) 2277–2291. doi: 10.1002/asia.201800647
11. [11]
  L. Chu, S. Zhu, F. Chen, F. Wang, L. Xu, Chin. J. Org. Chem. 42 (2022) 1–15. doi: 10.6023/cjoc202109002
12. [12]
  M. Yan, Y. Kawamata, P.S. Baran, Chem. Rev. 117 (2017) 13230–13319. doi: 10.1021/acs.chemrev.7b00397
13. [13]
  D.A. Thadathil, A. Varghese, K.V. Radhakrishnan, Asian J. Org. Chem. 10 (2021) 2820–2847. doi: 10.1002/ajoc.202100447
14. [14]
  Y. Chen, L.Q. Lu, D.G. Yu, C.J. Zhu, W.J. Xiao, Sci. China Chem. 62 (2018) 24–57.
15. [15]
  N. Chen, H.C. Xu, Green Synth. Catal. 2 (2021) 165–178. doi: 10.1016/j.gresc.2021.03.002
16. [16]
  X. Bao, J. Li, W. Jiang, C. Huo, Synthesis (Mass) 51 (2019) 4507–4530. doi: 10.1055/s-0039-1690987
17. [17]
  C. Chen, Nat. Rev. Chem. 2 (2018) 6–14. doi: 10.1038/s41570-018-0003-0
18. [18]
  Y. Li, D. Wu, H.G. Cheng, G. Yin, Angew. Chem. Int. Ed. 59 (2020) 7990–8003. doi: 10.1002/anie.201913382
19. [19]
  A. Vasseur, J. Bruffaerts, I. Marek, Nat. Chem. 8 (2016) 209–219. doi: 10.1038/nchem.2445
20. [20]
  S. Yang, Y. Chen, Z. Ding, Org. Biomol. Chem. 18 (2020) 6983–7001. doi: 10.1039/D0OB01323D
21. [21]
  H. Sommer, F. Julia-Hernandez, R. Martin, I. Marek, ACS Cent. Sci. 4 (2018) 153–165. doi: 10.1021/acscentsci.8b00005
22. [22]
  D.K. Wang, L. Li, Q. Xu, et al., Org. Chem. Front. 8 (2021) 7037–7049. doi: 10.1039/D1QO01002F
23. [23]
  M. Zhang, Y. Ji, C. Zhang, Chin. J. Chem. 40 (2022) 1608–1622. doi: 10.1002/cjoc.202200072
24. [24]
  K. Yang, Q. Song, Org. Lett. 18 (2016) 5460–5463. doi: 10.1021/acs.orglett.6b02527
25. [25]
  Z. Kuang, K. Yang, Q. Song, Org. Lett. 19 (2017) 2702–2705. doi: 10.1021/acs.orglett.7b01036
26. [26]
  W. Wang, C. Ding, H. Pang, G. Yin, Org. Lett. 21 (2019) 3968–3971. doi: 10.1021/acs.orglett.9b01120
27. [27]
  A.M.Y. Suliman, E.M.A. Ahmed, T.J. Gong, Y. Fu, Chem. Commun. 57 (2021) 6400–6403. doi: 10.1039/D1CC01620B
28. [28]
  Y. Deng, J. He, S. Cao, X. Qian, Chin. Chem. Lett. 33 (2022) 2363–2371. doi: 10.1016/j.cclet.2021.11.049
29. [29]
  E. Thiery, D. Harakat, J.L. Bras, J. Muzart, Organometallics 27 (2008) 3996–4004. doi: 10.1021/om8004433
30. [30]
  L. Li, T. Gong, X. Lu, B. Xiao, Y. Fu, Nat. Commun. 8 (2017) 345–351. doi: 10.1038/s41467-017-00363-4
31. [31]
  A.M. Bergmann, S.K. Dorn, K.B. Smith, K.M. Logan, M.K. Brown, Angew. Chem. Int. Ed. 58 (2019) 1719–1723. doi: 10.1002/anie.201812533
32. [32]
  Y. Ano, N. Kawai, N. Chatani, Chem. Sci. 12 (2021) 12326–12332. doi: 10.1039/D1SC02873A
33. [33]
  Y. He, Y. Cai, S. Zhu, J. Am. Chem. Soc. 139 (2017) 1061–1064. doi: 10.1021/jacs.6b11962
34. [34]
  Z. Li, D. Wu, C. Ding, G. Yin, CCS Chem. 2 (2020) 576–582.
35. [35]
  M. Orlandi, M.J. Hilton, E. Yamamoto, F.D. Toste, M.S. Sigman, J. Am. Chem. Soc. 139 (2017) 12688–12695. doi: 10.1021/jacs.7b06917
36. [36]
  W. Wang, C. Ding, Y. Li, et al., Angew. Chem. Int. Ed. 58 (2019) 4612–4616. doi: 10.1002/anie.201814572
37. [37]
  J. Mirý, C. d. Pozo, F.D. Toste, S. Fustero, Angew. Chem. Int. Ed. 55 (2016) 9045–9049. doi: 10.1002/anie.201603046
38. [38]
  H.M. Nelson, B.D. Williams, J. Miro, F.D. Toste, J. Am. Chem. Soc. 137 (2015) 3213–3216. doi: 10.1021/jacs.5b00344
39. [39]
  Y. Wang, X. Dong, R.C. Larock, J. Org. Chem. 68 (2003) 3090–3098. doi: 10.1021/jo026716p
40. [40]
  H. Pang, D. Wu, H. Cong, G. Yin, ACS Catal. 9 (2019) 8555–8560. doi: 10.1021/acscatal.9b02747
41. [41]
  R. Yu, R. Shanmugam, X. Fang, Angew. Chem. Int. Ed. 59 (2020) 21436–21441. doi: 10.1002/anie.202008854
42. [42]
  D. Zhu, Z. Jiao, Y.R. Chi, et al., Angew. Chem. Int. Ed. 59 (2020) 5341–5345. doi: 10.1002/anie.201915864
43. [43]
  Y.W. Chen, Y. Liu, H.Y. Lu, G.Q. Lin, Z.T. He, Nat. Commun. 12 (2021) 5626–5634. doi: 10.1038/s41467-021-25978-6
44. [44]
  H. Pang, D. Wu, G. Yin, Chin. J. Org. Chem. 41 (2021) 849–856. doi: 10.6023/cjoc202006022
45. [45]
  Y. Li, H. Pang, D. Wu, et al., Angew. Chem. Int. Ed. 58 (2019) 8872–8876. doi: 10.1002/anie.201903890
46. [46]
  S. Bera, R. Mao, X. Hu, Nat. Chem. 13 (2020) 270–277.
47. [47]
  C. Sun, G. Yin, Chin. Chem. Lett. 33 (2022) 5096–5100. doi: 10.1016/j.cclet.2022.04.026
48. [48]
  B.J. McCarty, W. Tang, Green Synth. Catal. 2 (2021) 1–3. doi: 10.1016/j.gresc.2020.12.004
49. [49]
  P. Basnet, R.K. Dhungana, S. Thapa, et al., J. Am. Chem. Soc. 140 (2018) 7782–7786. doi: 10.1021/jacs.8b03163
50. [50]
  X. Chen, W. Rao, T. Yang, M.J. Koh, Nat. Commun. 11 (2020) 5857–5865. doi: 10.1038/s41467-020-19717-6
51. [51]
  B. Du, Y. Ouyang, Q. Chen, W.Y. Yu, J. Am. Chem. Soc. 143 (2021) 14962–14968. doi: 10.1021/jacs.1c05834
52. [52]
  X.X. Wang, Y.T. Xu, Z.L. Zhang, X. Lu, Y. Fu, Nat. Commun. 13 (2022) 1890–1899. doi: 10.1038/s41467-022-29554-4
53. [53]
  F. Julia-Hernandez, T. Moragas, J. Cornella, R. Martin, Nature 545 (2017) 84–88. doi: 10.1038/nature22316
54. [54]
  Y. Zhang, J. He, P. Song, Y. Wang, S. Zhu, CCS Chem. 2 (2020) 2259–2268.
55. [55]
  J. Gao, M. Jiao, J. Ni, et al., Angew. Chem. Int. Ed. 60 (2021) 1883–1890. doi: 10.1002/anie.202011231
56. [56]
  Y. Li, H. Wei, G. Yin, Tetrahedron Lett. 100 (2022) 153889. doi: 10.1016/j.tetlet.2022.153889
57. [57]
  J.W. Wang, D.G. Liu, Z. Chang, et al., Angew. Chem. Int. Ed. 61 (2022) e202205537. doi: 10.1002/anie.202205537
58. [58]
  P.F. Yang, W. Shu, Angew. Chem. Int. Ed. 61 (2022) e202208018. doi: 10.1002/anie.202208018
59. [59]
  L. Zhao, Y. Zhu, M. Liu, et al., Angew. Chem. Int. Ed. 61 (2022) e202204716. doi: 10.1002/anie.202204716
60. [60]
  Y. Li, Y. Li, H. Shi, et al., Science 376 (2022) 749–753. doi: 10.1126/science.abn9124
61. [61]
  W. Wang, C. Ding, G. Yin, Nat. Catal. 3 (2020) 951–958. doi: 10.1038/s41929-020-00523-8
62. [62]
  B. Zhao, Y. Li, H. Li, et al., Sci. Bull. 66 (2020) 570–577.
63. [63]
  C. Ding, Y. Ren, C. Sun, J. Long, G. Yin, J. Am. Chem. Soc. 143 (2021) 20027–20034. doi: 10.1021/jacs.1c09214
64. [64]
  V. Saini, M. O'Dair, M.S. Sigman, J. Am. Chem. Soc. 137 (2015) 608–611. doi: 10.1021/ja511640g
65. [65]
  M. Cao, H. Xie, Chin. Chem. Lett. 32 (2021) 319–327. doi: 10.1016/j.cclet.2020.04.005
66. [66]
  D.G. Hall, Boronic Acids: Preparation and Applications in Organic Synthesis, Medicine and Materials, Wiley-VCH, Weinheim, 2011.
67. [67]
  W. Ming, X. Liu, L. Mao, X. Gu, Q. Ye, Chin. J. Chem. 39 (2021) 1716–1725. doi: 10.1002/cjoc.202000708
68. [68]
  S. Lessard, F. Peng, D.G. Hall, J. Am. Chem. Soc. 131 (2009) 9612–9613. doi: 10.1021/ja903946f
69. [69]
  G.E. Ferris, K. Hong, I.A. Roundtree, J.P. Morken, J. Am. Chem. Soc. 135 (2013) 2501–2504. doi: 10.1021/ja400506j
70. [70]
  G.Y. Fang, V.K. Aggarwal, Angew. Chem. Int. Ed. 46 (2007) 359–362. doi: 10.1002/anie.200603659
71. [71]
  N.J. Adamson, S.J. Malcolmson, ACS Catal. 10 (2019) 1060–1076.
72. [72]
  F. Schroeter, T. Strassner, Inorg. Chem. 57 (2018) 5159–5173. doi: 10.1021/acs.inorgchem.8b00175
73. [73]
  A. Domzalska-Pieczykolan, I. Funes-Ardoiz, B. Furman, C. Bolm, Angew. Chem. Int. Ed. 61 (2022) e202109801. doi: 10.1002/anie.202109801
74. [74]
  Y. Ye, J. Liu, B. Xu, et al., Chem. Sci. 12 (2021) 13209–13215. doi: 10.1039/D1SC04071E
75. [75]
  P. Zhang, C. Zou, Q. Zhao, C. Zhang, Org. Chem. Front. 8 (2021) 2589–2594. doi: 10.1039/D1QO00100K
76. [76]
  H. Shao, Y. Zhao, S. Wang, et al., Org. Lett. 24 (2022) 6520–6524. doi: 10.1021/acs.orglett.2c02416
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2. [2]
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