Citation: Haoran Shi, Jiaxin Wang, Yuqin Zhu, Hongyang Li, Guodong Ju, Lanlan Zhang, Chao Wang. Highly selective α-C(sp³)-H arylation of alkenyl amides via nickel chain-walking catalysis[J]. Chinese Chemical Letters, ;2024, 35(7): 109333. doi: 10.1016/j.cclet.2023.109333 shu

Highly selective α-C(sp³)-H arylation of alkenyl amides via nickel chain-walking catalysis

Tianjin Key Laboratory of Structure and Performance for Functional Molecules, College of Chemistry, Tianjin Normal University, Tianjin 300387, China

gdju@tjnu.edu.cn

chwang@tjnu.edu.cn

Received Date: 9 September 2023
Revised Date: 6 November 2023
Accepted Date: 16 November 2023
Available Online: 23 November 2023

Figures(4)

Herein, we report the migratory hydroarylation of unactivated alkenes with aryl iodides using native and weakly coordinating amide directors under mild conditions. Synergistic coordination of the monodentate directing group and the ligand enable the highly regioselective migratory hydroarylation via a chain walking process to form the thermodynamically stable five-membered nickelacyle intermediate. The protocol provides a variety of valuable α-aryl-substituted alkylamine products, and exhibited good functional group tolerance. The modification of bioactive compounds such as fenofibrate and indomethacin further highlights the synthetic value of this protocol.
- Alkenes,
- Hydroarylation,
- Chain-walking,
- Regioselective,
- Nickel catalysis
1. [1]
  A. Vasseur, J. Bruffaerts, I. Marek, Nat. Chem. 8 (2016) 209–219. doi: 10.1038/nchem.2445
2. [2]
  S.W.M. Crossley, C. Obradors, R.M. Martinez, R.A. Shenvi, Chem. Rev. 116 (2016) 8912–9000. doi: 10.1021/acs.chemrev.6b00334
3. [3]
  N.A. Eberhardt, H. Guan, Chem. Rev. 116 (2016) 8373–8426. doi: 10.1021/acs.chemrev.6b00259
4. [4]
  M.T. Pirnot, Y.M. Wang, S.L. Buchwald, Angew. Chem. Int. Ed. 55 (2016) 48–57. doi: 10.1002/anie.201507594
5. [5]
  H. Sommer, F. Juliá-Hernández, R. Martin, I. Marek, ACS Cent. Sci. 4 (2018) 153–165. doi: 10.1021/acscentsci.8b00005
6. [6]
  D. Janssen-Müller, B. Sahoo, S.Z. Sun, R. Martin, Isr. J. Chem. 60 (2020) 195–206. doi: 10.1002/ijch.201900072
7. [7]
  D. Fiorito, S. Scaringi, C. Mazet, Chem. Soc. Rev. 50 (2021) 1391–1406. doi: 10.1039/d0cs00449a
8. [8]
  Y. Wang, Y. He, S. Zhu, Acc. Chem. Res. 55 (2022) 3519–3536. doi: 10.1021/acs.accounts.2c00628
9. [9]
  Y. He, J. Chen, X. Jiang, S. Zhu, Chin. J. Chem. 2022 (40) 651–661. doi: 10.1002/cjoc.202100763
10. [10]
  Y. He, R. Tao, S. Zhu, Synlett 33 (2021) 224–230.
11. [11]
  Y. Schramm, M. Takeuchi, K. Semba, Y. Nakao, J.F. Hartwig, J. Am. Chem. Soc. 137 (2015) 12215–12218. doi: 10.1021/jacs.5b08039
12. [12]
  S.D. Friis, M.T. Pirnot, S.L. Buchwald, J. Am. Chem. Soc. 138 (2016) 8372–8375. doi: 10.1021/jacs.6b04566
13. [13]
  K. Semba, K. Ariyama, H. Zheng, et al., Angew. Chem. Int. Ed. 55 (2016) 6275–6279. doi: 10.1002/anie.201511975
14. [14]
  S.A. Green, J.L.M. Matos, A. Yagi, R.A. Shenvi, J. Am. Chem. Soc. 138 (2016) 12779–12782. doi: 10.1021/jacs.6b08507
15. [15]
  S.D. Friis, M.T. Pirnot, L.N. Dupuis, S.L. Buchwald, Angew. Chem. Int. Ed. 56 (2017) 7242–7246. doi: 10.1002/anie.201703400
16. [16]
  C. Wang, G. Xiao, T. Guo, et al., J. Am. Chem. Soc. 140 (2018) 9332–9336. doi: 10.1021/jacs.8b03619
17. [17]
  L.J. Xiao, L. Cheng, W.M. Feng, et al., Angew. Chem. Int. Ed. 57 (2018) 461–464. doi: 10.1002/anie.201710735
18. [18]
  H. Wang, Z. Bai, T. Jiao, et al., J. Am. Chem. Soc. 140 (2018) 3542–3546. doi: 10.1021/jacs.8b00641
19. [19]
  Y.G. Chen, B. Shuai, X.T. Xu, et al., J. Am. Chem. Soc. 141 (2019) 3395–3399. doi: 10.1021/jacs.8b13524
20. [20]
  H. Lv, H. Kang, B. Zhou, et al., Nat. Commun. 10 (2019) 5025. doi: 10.1038/s41467-019-12949-1
21. [21]
  N.I. Saper, A. Ohgi, D.W. Small, et al., Nat. Chem. 12 (2020) 276–283. doi: 10.1038/s41557-019-0409-4
22. [22]
  Z.Q. Li, Y. Fu, R. Deng, et al., Angew. Chem. Int. Ed. 59 (2020) 23306–23312. doi: 10.1002/anie.202010840
23. [23]
  L. Cheng, M.M. Li, M.L. Li, et al., CCS Chem. 4 (2021) 2612–2619.
24. [24]
  Y. He, H. Song, J. Chen, S. Zhu, Nat. Commun. 12 (2021) 638. doi: 10.1038/s41467-020-20888-5
25. [25]
  S. Cuesta-Galisteo, J. Schörgenhumer, X. Wei, E. Merino, C. Nevado, Angew. Chem. Int. Ed. 60 (2021) 1605–1609. doi: 10.1002/anie.202011342
26. [26]
  L. Zhang, C. Luo, H. Shi, et al., Chem. Commun. 58 (2022) 13511–13514. doi: 10.1039/D2CC04932E
27. [27]
  D.M. Wang, L.Q. She, Y. Wu, C. Zhu, P. Wang, Nat. Commun. 13 (2022) 6878. doi: 10.1038/s41467-022-34675-x
28. [28]
  Y. He, Y. Cai, S. Zhu, J. Am. Chem. Soc. 139 (2017) 1061–1064. doi: 10.1021/jacs.6b11962
29. [29]
  Y. He, J. Ma, H. Song, et al., Nat. Commun. 13 (2022) 2471. doi: 10.1038/s41467-022-30006-2
30. [30]
  Y. Zhang, B. Han, S. Zhu, Angew. Chem. Int. Ed. 58 (2019) 13860–13864. doi: 10.1002/anie.201907185
31. [31]
  S. Bera, X. Hu, Angew. Chem. Int. Ed. 58 (2019) 13854–13859. doi: 10.1002/anie.201907045
32. [32]
  Y. Zhang, J. Ma, J. Chen, et al., Chem 7 (2021) 3171–3188. doi: 10.1016/j.chempr.2021.10.015
33. [33]
  Y. He, B. Han, S. Zhu, Organometallics 40 (2021) 2253–2264. doi: 10.1021/acs.organomet.0c00819
34. [34]
  Y.C. Luo, C. Xu, X. Zhang, Chin. J. Chem. 38 (2020) 1371–1394. doi: 10.1002/cjoc.202000224
35. [35]
  J. Derosa, O. Apolinar, T. Kang, V.T. Tran, K.M. Engle, Chem. Sci. 11 (2020) 4287–4296. doi: 10.1039/c9sc06006e
36. [36]
  L.M. Wickham, R. Giri, Acc. Chem. Res. 54 (2021) 3415–3437. doi: 10.1021/acs.accounts.1c00329
37. [37]
  S. Zhu, X. Zhao, H. Li, L. Chu, Chem. Soc. Rev. 50 (2021) 10836–10856. doi: 10.1039/d1cs00399b
38. [38]
  B.C. Lee, C.F. Liu, L.Q.H. Lin, et al., Chem. Soc. Rev. 52 (2023) 2946–2991. doi: 10.1039/d2cs00972b
39. [39]
  J. Han, R. He, C. Wang, Chem. Catal. 3 (2023) 100690. doi: 10.1016/j.checat.2023.100690
40. [40]
  X. Chen, W. Rao, T. Yang, M.J. Koh, Nat. Commun. 11 (2020) 5857. doi: 10.1038/s41467-020-19717-6
41. [41]
  X.X. Wang, Y.T. Xu, Z.L. Zhang, X. Lu, Y. Fu, Nat. Commun. 13 (2022) 1890. doi: 10.1038/s41467-022-29554-4
42. [42]
  L. Zhao, Y. Zhu, M. Liu, et al., Angew. Chem. Int. Ed. 61 (2022) e202204716. doi: 10.1002/anie.202204716
43. [43]
  J.W. Wang, D.G. Liu, Z. Chang, et al., Angew. Chem. Int. Ed. 61 (2022) e202205537. doi: 10.1002/anie.202205537
44. [44]
  P.F. Yang, W. Shu, Angew. Chem. Int. Ed. 61 (2022) e202208018. doi: 10.1002/anie.202208018
45. [45]
  J.W. Wang, Z. Li, D. Liu, et al., J. Am. Chem. Soc. 145 (2023) 10411–10421. doi: 10.1021/jacs.3c02950
46. [46]
  J. Rodrigalvarez, H. Wang, R. Martin, J. Am. Chem. Soc. 145 (2023) 3869–3874. doi: 10.1021/jacs.2c12915
47. [47]
  X. Wang, J. Xue, Z.Q. Rong, J. Am. Chem. Soc. 145 (2023) 15456–15464. doi: 10.1021/jacs.3c03900
48. [48]
  C. Chen, W. Guo, D. Qiao, S. Zhu, Angew. Chem. Int. Ed. 62 (2023) e202308320. doi: 10.1002/anie.202308320
49. [49]
  B. Du, Y. Ouyang, Q. Chen, W.Y. Yu, J. Am. Chem. Soc. 143 (2021) 14962–14968. doi: 10.1021/jacs.1c05834
50. [50]
  Y. Hwang, S.B. Baek, D. Kim, S. Chang, J. Am. Chem. Soc. 144 (2022) 4277–4285. doi: 10.1021/jacs.2c00948
51. [51]
  C. Lee, H. Seo, J. Jeon, S. Hong, Nat. Commun. 12 (2021) 5657. doi: 10.1038/s41467-021-25696-z
52. [52]
  Song, Y. Luo, K. Wang, et al., ACS Catal. 13 (2023) 4409–4420. doi: 10.1021/acscatal.3c00238
53. [53]
  L. Xie, J. Liang, H. Bai, et al., ACS Catal. 13 (2023) 10041–10047. doi: 10.1021/acscatal.3c01845
54. [54]
  X. Yu, H. Zhao, S. Xi, et al., Nat. Catal. 3 (2020) 585–592. doi: 10.1038/s41929-020-0470-9
55. [55]
  T.C. Jankins, R. Martin-Montero, P. Cooper, R. Martin, K.M. Engle, J. Am. Chem. Soc. 143 (2021) 14981–14986. doi: 10.1021/jacs.1c07162
56. [56]
  Iiyama, K. Fukaya, Y. Yamaguchi, et al., Org. Lett. 24 (2022) 202–206. doi: 10.1021/acs.orglett.1c03851
57. [57]
  A.K. Ghosh, J. Takayama, Y. Aubin, et al., J. Med. Chem. 52 (2009) 5228–5240. doi: 10.1021/jm900611t
58. [58]
  D.S. Palacios, E. Meredith, T. Kawanami, et al., Med. Chem. Lett. 28 (2018) 365–370. doi: 10.1016/j.bmcl.2017.12.037
59. [59]
  Y. Zhao, J. Chen, Q. Liu, Y. Li, Molecules 25 (2020) 406. doi: 10.3390/molecules25020406
60. [60]
  J.H. Xie, S.F. Zhu, Q.L. Zhou, Chem. Rev. 111 (2011) 1713–1760. doi: 10.1021/cr100218m
61. [61]
  O.I. Afanasyev, E. Kuchuk, D.L. Usanov, D. Chusov, Chem. Rev. 119 (2019) 11857–11911. doi: 10.1021/acs.chemrev.9b00383
62. [62]
  A. Trowbridge, S.M. Walton, M.J. Gaunt, Chem. Rev. 120 (2020) 2613–2692. doi: 10.1021/acs.chemrev.9b00462
63. [63]
  K. Matsumura, H. Shimizu, T. Saito, H. Kumobayashi, Adv. Synth. Catal. 345 (2003) 180–184. doi: 10.1002/adsc.200390008
64. [64]
  J. Zhang, Y. Li, Z. Wang, K. Ding, Angew. Chem. Int. Ed. 50 (2011) 11743–11747. doi: 10.1002/anie.201104912
65. [65]
  Á. Chávez, S. Vargas, A. Suárez, E. Álvarez, A. Pizzano, Adv. Synth. Catal. 353 (2011) 2775–2794. doi: 10.1002/adsc.201000611
66. [66]
  T.X. Métro, J. Bonnamour, T. Reidon, et al., Chem. Commun. 48 (2012) 11781–11783. doi: 10.1039/c2cc36352f
67. [67]
  D.C. Lenstra, D.T. Nguyen, J. Mecinović, Tetrahedron 71 (2015) 5547–5553. doi: 10.1016/j.tet.2015.06.066
68. [68]
  A.W. Rand, H. Yin, L. Xu, et al., ACS Catal. 10 (2020) 4671–4676. doi: 10.1021/acscatal.0c01318
69. [69]
  X. Shu, D. Zhong, Y. Lin, X. Qin, H. Huo, J. Am. Chem. Soc. 144 (2022) 8797–8806. doi: 10.1021/jacs.2c02795
70. [70]
  Z. Li, L. Huan, J. Li, et al., Angew. Chem. Int. Ed. 62 (2023) e202305889. doi: 10.1002/anie.202305889
71. [71]
  S. Wang, C. Luo, L. Zhao, et al., Cell Rep. Phys. Sci. 2 (2021) 100574. doi: 10.1016/j.xcrp.2021.100574
72. [72]
  L. Xie, S. Wang, L. Zhang, et al., Nat. Commun. 12 (2021) 6280. doi: 10.1038/s41467-021-26527-x
73. [73]
  L. Zhao, X. Meng, Y. Zou, et al., Org. Lett. 23 (2021) 8516–8521. doi: 10.1021/acs.orglett.1c03210
74. [74]
  L. Zhu, X. Meng, L. Xie, et al., Org. Chem. Front. 9 (2022) 3068–3074. doi: 10.1039/d2qo00396a
75. [75]
  X. Meng, L. Zhu, J. Liang, et al., Org. Lett. 24 (2022) 6962–6967. doi: 10.1021/acs.orglett.2c02768
76. [76]
  Z.K. Zhang, Y.L. Feng, Z. Ruan, et al., Chem. Commun. 58 (2022) 11709–11712. doi: 10.1039/d2cc04382c
77. [77]
  J. Zhao, L. Bao, L. Zhu, et al., Org. Chem. Front. 9 (2022) 6556–6565. doi: 10.1039/d2qo01182d
78. [78]
  J. Han, Y. Tang, J. Huang, et al., Chin. J. Chem. 41 (2023) 631–636. doi: 10.1002/cjoc.202200647
79. [79]
  J. Diccianni, Q. Lin, T. Diao, Acc. Chem. Res. 53 (2020) 906–919. doi: 10.1021/acs.accounts.0c00032
80. [80]
  X. Lu, B. Xiao, Z. Zhang, et al., Nat. Commun. 7 (2016) 11129. doi: 10.1038/ncomms11129
81. [81]
  Y. Cheng, Z. Gui, R. Tao, Y. Wang, S. Zhu, Green Synth. Catal. 3 (2022) 377–379. doi: 10.1016/j.gresc.2022.03.009
82. [82]
  C. Sun, G. Yin, Chin. Chem. Lett. 33 (2022) 5096–5100. doi: 10.1016/j.cclet.2022.04.026
83. [83]
  S.X. Ni, Y.L. Li, H.Q. Ni, et al., Chin. Chem. Lett. 34 (2023) 107614. doi: 10.1016/j.cclet.2022.06.037
84. [84]
  G. Dong, S. Wang, Z. Miao, et al., J. Med. Chem. 55 (2012) 7593–7613. doi: 10.1021/jm300605m
85. [85]
  T. Cernak, K.D. Dykstra, S. Tyagarajan, P. Vachal, S.W. Krska, Chem. Soc. Rev. 45 (2016) 546–576. doi: 10.1039/C5CS00628G
1. [1]
  Zhenkang Ai , Hui Chen , Xuebin Liao . Nickel-catalyzed decarboxylative difluoromethylation and alkylation of alkenes. Chinese Chemical Letters, 2025, 36(3): 109954-. doi: 10.1016/j.cclet.2024.109954
2. [2]
  Jian Han , Li-Li Zeng , Qin-Yu Fei , Yan-Xiang Ge , Rong-Hui Huang , Fen-Er Chen . Recent advances in remote C(sp³)–H functionalization via chelating group-assisted metal-catalyzed chain-walking reaction. Chinese Chemical Letters, 2024, 35(11): 109647-. doi: 10.1016/j.cclet.2024.109647
3. [3]
  Wujun Jian , Mong-Feng Chiou , Yajun Li , Hongli Bao , Song Yang . Cu-catalyzed regioselective diborylation of 1,3-enynes for the efficient synthesis of 1,4-diborylated allenes. Chinese Chemical Letters, 2024, 35(5): 108980-. doi: 10.1016/j.cclet.2023.108980
4. [4]
  Junxin Li , Chao Chen , Yuzhen Dong , Jian Lv , Jun-Mei Peng , Yuan-Ye Jiang , Daoshan Yang . Ligand-promoted reductive coupling between aryl iodides and cyclic sulfonium salts by nickel catalysis. Chinese Chemical Letters, 2024, 35(11): 109732-. doi: 10.1016/j.cclet.2024.109732
5. [5]
  Er-Meng Wang , Ziyi Wang , Xu Ban , Xiaowei Zhao , Yanli Yin , Zhiyong Jiang . Chemoselective photocatalytic sulfenylamination of alkenes with sulfenamides via energy transfer. Chinese Chemical Letters, 2024, 35(12): 109843-. doi: 10.1016/j.cclet.2024.109843
6. [6]
  Hongjin Shi , Guoyin Yin , Xi Lu , Yangyang Li . Stereoselective synthesis of 2-deoxy-α-C-glycosides from glycals. Chinese Chemical Letters, 2024, 35(12): 109674-. doi: 10.1016/j.cclet.2024.109674
7. [7]
  Heng Yang , Zhijie Zhou , Conghui Tang , Feng Chen . Recent advances in heterogeneous hydrosilylation of unsaturated carbon-carbon bonds. Chinese Chemical Letters, 2024, 35(6): 109257-. doi: 10.1016/j.cclet.2023.109257
8. [8]
  Danqing Wu , Jiajun Liu , Tianyu Li , Dazhen Xu , Zhiwei Miao . Research Progress on the Simultaneous Construction of C—O and C—X Bonds via 1,2-Difunctionalization of Olefins through Radical Pathways. University Chemistry, 2024, 39(11): 146-157. doi: 10.12461/PKU.DXHX202403087
9. [9]
  Ruilong Geng , Lingzi Peng , Chang Guo . Dynamic kinetic stereodivergent transformations of propargylic ammonium salts via dual nickel and copper catalysis. Chinese Chemical Letters, 2024, 35(8): 109433-. doi: 10.1016/j.cclet.2023.109433
10. [10]
  Kun Tang , Fen Su , Shijie Pan , Fengfei Lu , Zhongfu Luo , Fengrui Che , Xingxing Wu , Yonggui Robin Chi . Enones from aldehydes and alkenes by carbene-catalyzed dehydrogenative couplings. Chinese Chemical Letters, 2024, 35(9): 109495-. doi: 10.1016/j.cclet.2024.109495
11. [11]
  Boqiang Wang , Yongzhuo Xu , Jiajia Wang , Muyang Yang , Guo-Jun Deng , Wen Shao . Transition-metal free trifluoromethylimination of alkenes enabled by direct activation of N-unprotected ketimines. Chinese Chemical Letters, 2024, 35(9): 109502-. doi: 10.1016/j.cclet.2024.109502
12. [12]
  Yunqiang Li , Yongxian Huang , Sinuo Li , He Huang , Zhiwei Jiao . Elaborating azaaryl alkanes enabled by photoredox/palladium dual catalyzed dialkylation of azaaryl alkenes. Chinese Chemical Letters, 2025, 36(4): 110051-. doi: 10.1016/j.cclet.2024.110051
13. [13]
  Xiao-Ming Chen , Lianhui Song , Jun Pan , Fei Zeng , Yi Xie , Wei Wei , Dong Yi . Visible-light-induced four-component difunctionalization of alkenes to construct phosphorodithioate-containing quinoxalin-2(1H)-ones. Chinese Chemical Letters, 2024, 35(11): 110112-. doi: 10.1016/j.cclet.2024.110112
14. [14]
  Huaixiang Yang , Miao-Miao Li , Aijun Zhang , Jiefei Guo , Yongqi Yu , Wei Ding . Visible-light-induced photocatalyst- and metal-free radical phosphinoyloximation of alkenes with tert-butyl nitrite as bifunctional reagent. Chinese Chemical Letters, 2025, 36(3): 110425-. doi: 10.1016/j.cclet.2024.110425
15. [15]
  Conghui Wang , Lei Xu , Zhenhua Jia , Teck-Peng Loh . Recent applications of macrocycles in supramolecular catalysis. Chinese Chemical Letters, 2024, 35(4): 109075-. doi: 10.1016/j.cclet.2023.109075
16. [16]
  Wei Chen , Pieter Cnudde . A minireview to ketene chemistry in zeolite catalysis. Chinese Journal of Structural Chemistry, 2024, 43(11): 100412-100412. doi: 10.1016/j.cjsc.2024.100412
17. [17]
  Lin Zhang , Chaoran Li , Thongthai Witoon , Xingda An , Le He . Nano-thermometry in photothermal catalysis. Chinese Journal of Structural Chemistry, 2025, 44(4): 100456-100456. doi: 10.1016/j.cjsc.2024.100456
18. [18]
  Yu Mao , Yilin Liu , Xiaochen Wang , Shengyang Ni , Yi Pan , Yi Wang . Acylfluorination of enynes via phosphine and silver catalysis. Chinese Chemical Letters, 2024, 35(8): 109443-. doi: 10.1016/j.cclet.2023.109443
19. [19]
  Jiaqi Jia , Kathiravan Murugesan , Chen Zhu , Huifeng Yue , Shao-Chi Lee , Magnus Rueping . Multiphoton photoredox catalysis enables selective hydrodefluorinations. Chinese Chemical Letters, 2025, 36(2): 109866-. doi: 10.1016/j.cclet.2024.109866
20. [20]
  Xiao-Bo Liu , Ren-Ming Liu , Xiao-Di Bao , Hua-Jian Xu , Qi Zhang , Yu-Feng Liang . Nickel-catalyzed reductive formylation of aryl halides via formyl radical. Chinese Chemical Letters, 2024, 35(12): 109783-. doi: 10.1016/j.cclet.2024.109783

Get Citation

PDF

XML

Metrics

PDF Downloads(2)
Abstract views(264)
HTML views(4)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

Highly selective α-C(sp3)-H arylation of alkenyl amides via nickel chain-walking catalysis

Metrics

通讯作者: 陈斌, bchen63@163.com

Highly selective α-C(sp³)-H arylation of alkenyl amides via nickel chain-walking catalysis