Citation: Ning Zhao, Xiaojiao Jin, Yanfeng Dang. Exploring the pivotal role of silver(I) additives in palladium-catalyzed NH₂-directed C(sp³)-H arylation reactions[J]. Chinese Chemical Letters, ;2021, 32(12): 3980-3983. doi: 10.1016/j.cclet.2021.04.044 shu

Exploring the pivotal role of silver(I) additives in palladium-catalyzed NH₂-directed C(sp³)-H arylation reactions

Tianjin Key Laboratory of Molecular Optoelectronic Sciences, Department of Chemistry, Tianjin University, Tianjin 300072, China

yanfeng.dang@tju.edu.cn

Received Date: 7 March 2021
Revised Date: 20 April 2021
Accepted Date: 22 April 2021
Available Online: 28 April 2021

Figures(5)

Combined theoretical and experimental studies have explained the mechanism of Pd-catalyzed δ-C(sp³)−H arylation of primary amines. Instead of the monomeric Pd mechanism, our research unveils that all steps including C-H activation, oxidative addition, and reductive elimination take place via the heterodimeric Pd-Ag intermediates and transition states. Experimentally, the active heterodimeric Pd-Ag species were detected by mass spectrometry, which further confirms the proposed heterodimeric mechanism. Insight gained through this study reveals the synergistic manner of palladium catalysis and silver(I) additives in native NH₂-directed C‒H activation and C-C coupling reactions.
- Palladium catalysis,
- Silver(I) additive,
- C(sp³)-H arylation,
- Heterodimeric mechanism,
- DFT study
1. [1]
  X. Chen, K.M. Engle, D.H. Wang, J.Q. Yu, Angew. Chem. Int. Ed. 48 (2009) 5094-5115. doi: 10.1002/anie.200806273
2. [2]
  K.M. Engle, T.S. Mei, M. Wasa, J.Q. Yu, Acc. Chem. Res. 45 (2012) 788-802. doi: 10.1021/ar200185g
3. [3]
  (a) J. He, M. Wasa, K.S.L. Chan, Q. Shao, J.Q. Yu, Chem. Rev. 117 (2017) 8754-8786;
  (b) J. Huang, Q. Gu, S.L. You, Chin. J. Org. Chem. 38 (2018) 51-61;
  (c) L. Xu, H. Xu, H. Lin, H. Dai, Chin. J. Org. Chem. 38 (2018) 1940-1948;
  (d) Q. Ren, B. Nie, Y. Zhang, J. Zhang, Chin. J. Org. Chem. 38 (2018) 2465-2490;
  (e) K. Zhao, L. Yang, J. Liu, C. Xia, Chin. J. Org. Chem. 38 (2018) 2833-2857;
  (f) Y.H. Liu, Y.N. Xia, B.F. Shi, Chin. J. Chem. 38 (2020) 635-662;
  (g) B. Ni, H. Cölfen, SmartMat 2 (2021) 17-32.
4. [4]
  (a) C. Shan, L. Zhu, L.B. Qu, R. Bai, Y. Lan, Chem. Soc. Rev. 47 (2018) 7552-7576;
  (b) M.M. Chen, L.Y. Shao, L.J. Lun, et al., Chin. Chem. Lett. 30 (2019) 702-706;
  (c) X.L. Han, P.P. Lin, Q. Li, Chin. Chem. Lett. 30 (2019) 1495-1502;
  (d) Y. Wu, B. Shi, Chin. J. Org. Chem. 40 (2020) 3517-3535.
5. [5]
  (a) F.L. Zhang, K. Hong, T.J. Li, H. Park, J.Q. Yu, Science 351 (2016) 252-256;
  (b) W. Liu, J. Zheng, Z. Liu, W. Hu, X. Wang, Y. Dang, ACS Catal. 8 (2018) 7698-7709.
6. [6]
  X. Jin, H. Xu, N. Zhao, R. Li, Y. Dang, Org. Lett. 22 (2020) 1464-1468.
7. [7]
  G. He, Y.S. Zhao, S.Y. Zhang, C.X. Lu, G. Chen, J. Am. Chem. Soc. 134 (2012), 3-6. doi: 10.1021/ja210660g
8. [8]
  E.T. Nadres, O. Daugulis, J. Am. Chem. Soc. 134 (2012) 7-10. doi: 10.1021/ja210959p
9. [9]
  (a) J.W. Xu, Z.Z. Zhang, W.H. Rao, B.F. Shi, J. Am. Chem. Soc. 138 (2016) 10750-10753;
  (b) B.B. Zhan, Y. Li, J.W. Xu, et al., Angew. Chem. Int. Ed. 57 (2018) 5858-5862.
10. [10]
  W. Cui, S.W. Chen, J.Q. Wu, et al., Org. Lett. 16 (2014) 4288-4291. doi: 10.1021/ol502011k
11. [11]
  (a) A. McNally, B. Haffemayer, B.S.L. Collins, M.J. Gaunt, Nature 510 (2014) 129-133;
  (b) J. Calleja, D. Pla, T.W. Gorman, V. Domingo, B. Haffemayer, M.J. Gaunt, Nat. Chem. 7 (2015) 1009-1016;
  (c) Y. Liu, H. Ge, Nat. Chem. 9 (2017) 26-32.
12. [12]
  H. Lin, X. Pan, A.L. Barsamian, T.M. Kamenecka, T.D. Bannister, ACS Catal. 9 (2019) 4887-4891. doi: 10.1021/acscatal.8b04927
13. [13]
  Y.F. Yang, G.J. Cheng, P. Liu, et al., J. Am. Chem. Soc. 136 (2014) 344-355. doi: 10.1021/ja410485g
14. [14]
  M. Anand, R.B. Sunoj, H.F. Schaefer, J. Am. Chem. Soc. 136 (2014) 5535-5538. doi: 10.1021/ja412770h
15. [15]
  W. Feng, T. Wang, D. Liu, X. Wang, Y. Dang, ACS Catal. 9 (2019) 6672-6680. doi: 10.1021/acscatal.9b01412
16. [16]
  D. Balcells, E. Clot, O. Eisenstein, Chem. Rev. 110 (2010) 749-823. doi: 10.1021/cr900315k
17. [17]
  D. Lapointe, K. Fagnou, Chem. Lett. 39 (2010) 1118-1126. doi: 10.1246/cl.2010.1118
18. [18]
  D.L. Davies, S.A. Macgregor, C.L. McMullin, Chem. Rev. 117 (2017) 8649-8709. doi: 10.1021/acs.chemrev.6b00839
19. [19]
  Y.F. Yang, X. Hong, J.Q. Yu, K.N. Houk, Acc. Chem. Res. 50 (2017) 2853-2860. doi: 10.1021/acs.accounts.7b00440
20. [20]
  D.L. Davies, S.M.A. Donald, S. Macgregor, J. Am. Chem. Soc. 127 (2005) 13754-13755. doi: 10.1021/ja052047w
21. [21]
  A. Bondi, J. Phys. Chem. 68 (1964), 441-451. doi: 10.1021/j100785a001
22. [22]
  J.E. Kickham, S.J. Loeb, Organometallics 14 (1995) 3584-3587. doi: 10.1021/om00007a071
23. [23]
  P. Braunstein, C. Frison, N. Oberbeckmann-Winter, et al., Angew. Chem. Int. Ed. 43 (2004) 6120-6125. doi: 10.1002/anie.200461291
24. [24]
  J. Vicente, A. Arcas, F. Julia-Hernandez, D. Bautista, Angew. Chem. Int. Ed. 50 (2011) 6896-6899. doi: 10.1002/anie.201102214
25. [25]
  Y. Dang, S. Qu, J.W. Nelson, et al., J. Am. Chem. Soc. 137 (2015) 2006-2014. doi: 10.1021/ja512374g
26. [26]
  Y.F. Yang, X. Hong, G. Chen, J.Q. Yu, K.N. Houk, J. Am. Chem. Soc. 139 (2017) 8514-8521. doi: 10.1021/jacs.7b01801
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Exploring the pivotal role of silver(I) additives in palladium-catalyzed NH2-directed C(sp3)-H arylation reactions

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通讯作者: 陈斌, bchen63@163.com

Exploring the pivotal role of silver(I) additives in palladium-catalyzed NH₂-directed C(sp³)-H arylation reactions