Citation: Pengfei Zhang, Qingxue Ma, Zhiwei Jiang, Xiaohua Xu, Zhong Jin. Transition-metal-catalyzed remote meta-C—H alkylation and alkynylation of aryl sulfonic acids enabled by an indolyl template[J]. Chinese Chemical Letters, ;2024, 35(8): 109361. doi: 10.1016/j.cclet.2023.109361 shu

Transition-metal-catalyzed remote meta-C—H alkylation and alkynylation of aryl sulfonic acids enabled by an indolyl template

Pengfei Zhang ^a ,
Qingxue Ma ^a ,
Zhiwei Jiang ^a ,
Xiaohua Xu ^{a, *,} ,
Zhong Jin ^{a, b, *,}

a.
College of Chemistry, State Key Laboratory of Elemento-organic Chemistry, Nankai University, Tianjin 300071, China
b.
Key Laboratory of Xinjiang Native Medicinal and Edible Plant Resource Chemistry, College of Chemistry and Environmental Sciences, Kashi University, Kashgar 844007, China

xiaohuaxu@nankai.edu.cn

zjin@nankai.edu.cn

Received Date: 9 September 2023
Revised Date: 23 November 2023
Accepted Date: 3 December 2023
Available Online: 6 December 2023

Figures(6)

Transition-metal-catalyzed remote sp²C—H functionalization of aryl sulfonic acids was hardly ever realized owing to competitive ortho-C—H functionalization of aryl sulfonates and electron-deficient nature of phenyl ring. Herein, with the assistance of a practical biaryl indolyl directing template, palladium-catalyzed remote sp²C—H alkylation of aryl sulfonic acids have been achieved in moderate to good yields with exclusive meta selectivity. Moreover, remote meta-selective C—H alkynylation of aryl sulfonic acids was also accomplished with a rhodium catalyst. These meta-C—H functionalized products proved to be the superior synthetic precursors, which are difficult to access using the conventional strategy.
- C—H functionalization,
- Aryl sulfonic acid,
- Site-selectivity,
- Transition-metal catalysis,
- Alkylation,
- Alkynylation
1. [1]
  H.J. Xu, Y. Lu, M.E. Farmer, et al., J. Am. Chem. Soc. 139 (2017) 2200–2203. doi: 10.1021/jacs.6b13269
2. [2]
  Z. Huang, G. Dong, Acc. Chem. Res. 50 (2017) 465–471. doi: 10.1021/acs.accounts.6b00476
3. [3]
  L. Ackermann, Acc. Chem. Res. 47 (2014) 281–295. doi: 10.1021/ar3002798
4. [4]
  P.B. Arockiam, C. Bruneau, P.H. Dixneuf, Chem. Rev. 112 (2012) 5879–5918. doi: 10.1021/cr300153j
5. [5]
  X. Chen, K.M. Engle, D.H. Wang, J.Q. Yu, Angew. Chem. Int. Ed. 48 (2009) 5094–5115. doi: 10.1002/anie.200806273
6. [6]
  O. Daugulis, H.Q. Do, D. Shabashov, Acc. Chem. Res. 42 (2009) 1074–1086. doi: 10.1021/ar9000058
7. [7]
  K.M. Engle, J.Q. Yu, J. Org. Chem. 78 (2013) 8927–8955. doi: 10.1021/jo400159y
8. [8]
  R. Giri, S. Thapa, A. Kafle, Adv. Synth. Catal. 356 (2014) 1395–1411. doi: 10.1002/adsc.201400105
9. [9]
  Z. Huang, H.N. Lim, F. Mo, M.C. Young, G. Dong, Chem. Soc. Rev. 44 (2015) 7764–7786. doi: 10.1039/C5CS00272A
10. [10]
  T.W. Lyons, M.S. Sanford, Chem. Rev. 110 (2010) 1147–1169. doi: 10.1021/cr900184e
11. [11]
  S.R. Neufeldt, M.S. Sanford, Acc. Chem. Res. 45 (2012) 936–946. doi: 10.1021/ar300014f
12. [12]
  M.P. Drapeau, L.J. Gooßen, Chem. Eur. J. 22 (2016) 18654–18677. doi: 10.1002/chem.201603263
13. [13]
  A. Ros, R. Fernandez, J.M. Lassaletta, Chem. Soc. Rev. 43 (2014) 3229–3243. doi: 10.1039/C3CS60418G
14. [14]
  T. Satoh, M. Miura, Synthesis 20 (2010) 3395–3409. doi: 10.1055/s-0030-1258225
15. [15]
  G. Shi, Y. Zhang, Adv. Synth. Catal. 356 (2014) 1419–1442. doi: 10.1002/adsc.201400028
16. [16]
  D.A. Colby, R.G. Bergman, J.A. Ellman, Chem. Rev. 110 (2010) 624–655. doi: 10.1021/cr900005n
17. [17]
  D.A. Colby, A.S. Tsai, R.G. Bergman, J.A. Ellman, Acc. Chem. Res. 45 (2012) 814–825. doi: 10.1021/ar200190g
18. [18]
  G. Rouquet, N. Chatani, Angew. Chem. Int. Ed. 52 (2013) 11726–11743. doi: 10.1002/anie.201301451
19. [19]
  K.M. Engle, T.S. Meit, M. Wasa, J.Q. Yu, Acc. Chem. Res. 45 (2012) 788–802. doi: 10.1021/ar200185g
20. [20]
  H. Shi, P. Wang, S. Suzuki, M.E. Farmer, J.Q. Yu, J. Am. Chem. Soc. 138 (2016) 14876–14879. doi: 10.1021/jacs.6b11055
21. [21]
  H.J. Xu, Y.S. Kang, H. Shi, et al., J. Am. Chem. Soc. 141 (2019) 76–79. doi: 10.1021/jacs.8b11038
22. [22]
  S. Lee, H. Lee, K.L. Tan, J. Am. Chem. Soc. 135 (2013) 18778–18781. doi: 10.1021/ja4107034
23. [23]
  B.E. Haines, Y. Saito, Y. Segawa, K. Itami, D.G. Musaev, ACS Catal. 6 (2016) 7536–7546. doi: 10.1021/acscatal.6b02317
24. [24]
  M.E. Hoque, R. Bisht, C. Haldar, B. Chattopadhyay, J. Am. Chem. Soc. 139 (2017) 7745–7748. doi: 10.1021/jacs.7b04490
25. [25]
  J.A. Leitch, C.L. McMullin, A.J. Paterson, et al., Angew. Chem. Int. Ed. 56 (2017) 15131–15135. doi: 10.1002/anie.201708961
26. [26]
  D. Leow, G. Li, T.S. Mei, J.Q. Yu, Nature 486 (2012) 518–522. doi: 10.1038/nature11158
27. [27]
  H.X. Dai, G. Li, X.G. Zhang, A.F. Stepan, J.Q. Yu, J. Am. Chem. Soc. 135 (2013) 7567–7571. doi: 10.1021/ja400659s
28. [28]
  L. Wan, N. Dastbaravardey, G. Li, J.Q. Yu, J. Am. Chem. Soc. 135 (2013) 18056–18059. doi: 10.1021/ja410760f
29. [29]
  R.Y. Tang, G. Li, J.Q. Yu, Nature 507 (2014) 215–220. doi: 10.1038/nature12963
30. [30]
  G. Yang, P. Lindovska, D. Zhu, et al., J. Am. Chem. Soc. 136 (2014) 10807–10813. doi: 10.1021/ja505737x
31. [31]
  L. Chu, M. Shang, K. Tanaka, et al., ACS Cent. Sci. 1 (2015) 394–399. doi: 10.1021/acscentsci.5b00312
32. [32]
  Y. Deng, J.Q. Yu, Angew. Chem. Int. Ed. 54 (2015) 888–891. doi: 10.1002/anie.201409860
33. [33]
  M. Bera, A. Maji, S.K. Sahoo, D. Maiti, Angew. Chem. Int. Ed. 54 (2015) 8515–8519. doi: 10.1002/anie.201503112
34. [34]
  S. Bag, R. Jayarajan, R. Mondal, D. Maiti, Angew. Chem. Int. Ed. 56 (2017) 3182–3186. doi: 10.1002/anie.201611360
35. [35]
  S. Bag, R. Jayarajan, U. Dutta, et al., Angew. Chem. Int. Ed. 56 (2017) 12538–12542. doi: 10.1002/anie.201706360
36. [36]
  L. Zhang, C. Zhao, Y. Liu, et al., Angew. Chem. Int. Ed. 56 (2017) 12245–12249. doi: 10.1002/anie.201705495
37. [37]
  Z. Zhang, K. Tanaka, J.Q. Yu, Nature 543 (2017) 538–542. doi: 10.1038/nature21418
38. [38]
  T.K. Achar, X. Zhang, R. Mondal, et al., Angew. Chem. Int. Ed. 58 (2019) 10353–10360. doi: 10.1002/anie.201904608
39. [39]
  S. Li, H. Wang, Y. Weng, G. Li, Angew. Chem. Int. Ed. 58 (2019) 18502–18507. doi: 10.1002/anie.201910691
40. [40]
  S. Porey, X. Zhang, S. Bhowmick, et al., J. Am. Chem. Soc. 142 (2020) 3762–3774. doi: 10.1021/jacs.9b10646
41. [41]
  A.F. Williams, A.J.P. White, A.C. Spivey, C.J. Cordier, Chem. Sci. 11 (2020) 3301–3306. doi: 10.1039/d0sc00230e
42. [42]
  S. Bag, S. K, A. Mondal, J. Am. Chem. Soc. 142 (2020) 12453–12466. doi: 10.1021/jacs.0c05223
43. [43]
  S. Bag, S. Jana, S. Pradhan, et al., Nat. Commun. 12 (2021) 1393. doi: 10.1038/s41467-021-21633-2
44. [44]
  S. Bag, T. Patra, A. Modak, et al., J. Am. Chem. Soc. 137 (2015) 11888–11891. doi: 10.1021/jacs.5b06793
45. [45]
  T. Patra, S. Bag, R. Kancherla, et al., Angew. Chem. Int. Ed. 55 (2016) 7751–7755. doi: 10.1002/anie.201601999
46. [46]
  A. Maji, S. Guin, S. Feng, et al., Angew. Chem. Int. Ed. 56 (2017) 14903–14907. doi: 10.1002/anie.201708449
47. [47]
  A. Maji, A. Dahiya, G. Lu, et al., Nat. Commun. 9 (2018) 3582. doi: 10.1038/s41467-018-06018-2
48. [48]
  X. Chen, S. Fan, M. Zhang, et al., Chem. Sci. 12 (2021) 4126–4131. doi: 10.1039/d0sc07042d
49. [49]
  G. Meng, N.Y.S. Lam, E.L. Lucas, et al., J. Am. Chem. Soc. 142 (2020) 10571–10591. doi: 10.1021/jacs.0c04074
50. [50]
  Y.F. Yang, G.J. Cheng, P. Liu, et al., J. Am. Chem. Soc. 136 (2014) 344–355. doi: 10.1021/ja410485g
51. [51]
  S. Li, L. Cai, H. Ji, L. Yang, G. Li, Nat. Commun. 7 (2016) 10443. doi: 10.1038/ncomms10443
52. [52]
  L. Fang, T.G. Saint-Denis, B.L.H. Taylor, et al., J. Am. Chem. Soc. 139 (2017) 10702–10714. doi: 10.1021/jacs.7b03296
53. [53]
  L. Cai, S. Li, C. Zhou, G. Li, Org. Lett. 22 (2020) 7791–7796. doi: 10.1021/acs.orglett.0c02528
54. [54]
  S. Li, C. Zhang, L. Fu, et al., CCS Chem. 4 (2022) 1889–1900. doi: 10.31635/ccschem.021.202101156
55. [55]
  M. Liu, L.J. Li, J. Zhang, H. Xu, H.X. Dai, Chin. Chem. Lett. 31 (2020) 1301–1304. doi: 10.1016/j.cclet.2019.09.057
56. [56]
  W. Chang, Y. Wang, Y. Chen, J. Ma, Y. Liang, Chin. Chem. Lett. 34 (2023) 10879.
57. [57]
  M.V. Pham, B. Ye, N. Cramer, Angew. Chem. Int. Ed. 51 (2012) 10610–10614. doi: 10.1002/anie.201206191
58. [58]
  Y. Ran, Y. Yang, H. You, J. You, ACS Catal. 8 (2018) 1796–1801. doi: 10.1021/acscatal.7b04298
59. [59]
  Y. Dong, X. Zhang, J. Chen, et al., Chem. Sci. 10 (2019) 8744–8751. doi: 10.1039/c9sc03691a
60. [60]
  H.X. Dai, A.F. Stepan, M.S. Plummer, Y.H. Zhang, J.Q. Yu, J. Am. Chem. Soc. 133 (2011) 7222–7228. doi: 10.1021/ja201708f
61. [61]
  G. Wu, W. Ouyang, Q. Chen, Y. Huo, X. Li, Org. Chem. Front. 6 (2019) 284–289. doi: 10.1039/c8qo01105b
62. [62]
  T. Lan, L. Wang, Y. Rao, Org. Lett. 19 (2017) 972–975. doi: 10.1021/acs.orglett.6b03510
63. [63]
  S. Rej, N. Chatani, Chem. Sci. 11 (2020) 389–395. doi: 10.1039/c9sc04308j
64. [64]
  W. Liu, D. Wang, Y. Zhao, F. Yi, J. Chen, Adv. Synth. Catal. 358 (2016) 1968–1974. doi: 10.1002/adsc.201501104
65. [65]
  S. Feng, S. Li, J. Li, J. Wei, Org. Chem. Front. 6 (2019) 517–522. doi: 10.1039/c8qo01311j
66. [66]
  S. Ojha, N. Panda, Adv. Synth. Catal. 362 (2020) 561–571. doi: 10.1002/adsc.201900989
67. [67]
  K. Parthasarathy, C. Bolm, Chem. Eur. J. 20 (2014) 4896–4900. doi: 10.1002/chem.201304925
68. [68]
  W.J. Kerr, M. Reid, T. Tuttle, ACS Catal. 5 (2015) 402–410. doi: 10.1021/cs5015755
69. [69]
  R. Vanjari, T. Guntreddi, K.N. Singh, Chem. Asian J. 11 (2016) 696–699. doi: 10.1002/asia.201501385
70. [70]
  F. Li, T.X. Liu, G.W. Wang, Org. Lett. 14 (2012) 2176–2179. doi: 10.1021/ol3007452
71. [71]
  Y. Dong, G. Liu, Chem. Commun. 49 (2013) 8066–8068. doi: 10.1039/c3cc44690e
72. [72]
  Z. Qi, M. Wang, X. Li, Chem. Commun. 50 (2014) 9776–9778. doi: 10.1039/C4CC03627A
73. [73]
  W. Ma, R. Mei, G. Tenti, L. Ackermann, Chem. Eur. J. 20 (2014) 15248–15251. doi: 10.1002/chem.201404604
74. [74]
  N.Y.S. Lam, Z. Fan, K. Wu, et al., J. Am. Chem. Soc. 144 (2022) 2793–2803. doi: 10.1021/jacs.1c12654
75. [75]
  P. Zhang, Z. Jiang, Z. Fan, et al., Chem. Sci. 14 (2023) 8279–8287. doi: 10.1039/d3sc01670f
76. [76]
  S.B. Ankade, A.B. Shabade, V. Soni, B. Punji, ACS Catal. 11 (2021) 3268–3292. doi: 10.1021/acscatal.0c05580
77. [77]
  L. Ackermann, Chem. Rev. 111 (2011) 1315–1345. doi: 10.1021/cr100412j
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