Citation: Li Gang, Chen Ye, Xia Jibao. Progress on Transition-Metal-Catalyzed Cross-Coupling Reactions of Ammonium Salts via C-N Bond Cleavage[J]. Chinese Journal of Organic Chemistry, ;2018, 38(8): 1949-1962. doi: 10.6023/cjoc201803013 shu

Progress on Transition-Metal-Catalyzed Cross-Coupling Reactions of Ammonium Salts via C-N Bond Cleavage

Li Gang ^a,b ,
Chen Ye ^a,, ,
Xia Jibao ^b,,

a.
School Chemistry of Chemical Engineering, Guizhou University, Guiyang 550025
b.
State Key Laboratory for Oxo Synthesis and Selective Oxidation, Suzhou Research Institute of LICP, Lanzhou Institute of Chemical Physics(LICP), Chinese Academy of Sciences, Lanzhou 730000

Corresponding author: Chen Ye, ychen19@gzu.edu.cn Xia Jibao, jibaoxia@licp.cas.cn
Received Date: 12 March 2018
Revised Date: 8 April 2018
Available Online: 27 August 2018
Fund Project: Project supported by the National Natural Science Foundation of China (Nos. 21702212, 21772208, 21602230) and the Natural Science Foundation of Jiangsu Province (No. BK20161260)the National Natural Science Foundation of China 21602230the National Natural Science Foundation of China 21702212the Natural Science Foundation of Jiangsu Province BK20161260the National Natural Science Foundation of China 21772208

Figures(5)

Amines containing carbon-nitrogen (C-N) bonds are widely distributed in natural products, drug molecules and functional materials.C-N bonds are one of the most abundant and inert bonds in organic molecules.Selective cleavage of C-N bonds to construct carbon-carbon (C-C) and carbon-heteroatom (C-X) bonds represents a new synthetic method in organic synthesis.It is difficult for the direct cleavage of C-N bond.Ammonium salts are a series of stable compounds easily obtained from amines.The recent progress of transition-metal-catalyzed cross-coupling reactions via C-N bond cleavage using ammonium salts as starting materials is summerized.
- transition-metal-catalysis,
- ammonium salt,
- cross-coupling reaction,
- C-N bond cleavage
1. [1]
  (a) Paul, F. ; Patt, J. ; Hartwig, J. F. J. Am. Chem. Soc. 1994, 116, 5969.
  (b) Guram, A. S. ; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 7901.
  (c) Muci, A. R. ; Buchwald, S. L. Top. Curr. Chem. 2002, 219, 131.
  (d) Hartwig, J. F. Acc. Chem. Res. 2008, 41, 1534.
2. [2]
  (a) Blanksby, S. J. ; Ellison, G. B. Acc. Chem. Res. 2003, 36, 255.
  (b) Yao, X. -Q. ; Hou, X. -J. ; Jiao, H. ; Xiang, H. -W. ; Li, Y. -W. J. Phys. Chem. A 2003, 107, 9991.
3. [3]
  (a) Bonanno, J. B. ; Henry, T. P. ; Neithamer, D. R. ; Wolczanski, P. T. ; Lobkovsky, E. B. J. Am. Chem. Soc. 1996, 118, 5132.
  (b) Ueno, S. ; Chatani, N. ; Kakiuchi, F. J. Am. Chem. Soc. 2007, 129, 6098.
  (c) Koreeda, T. ; Kochi, T. ; Kakiuchi, F. J. Am. Chem. Soc. 2009, 131, 7238.
  (d) Tobisu, M. ; Nakamura, K. ; Chatani, N. J. Am. Chem. Soc. 2014, 136, 5587.
  (e) Zhao, Y. ; Snieckus, V. Org. Lett. 2014, 16, 3200.
  (f) Cong, X. ; Fan, F. ; Ma, P. ; Luo, M. ; Chen, H. ; Zeng, X. J. Am. Chem. Soc. 2017, 139, 15182.
4. [4]
  (a) Geng, W. ; Zhang, W. -X. ; Hao, W. ; Xi, Z. J. Am. Chem. Soc. 2012, 134, 20230.
  (b) Xie, Y. ; Hu, J. ; Wang, Y. ; Xia, C. ; Huang, H. J. Am. Chem. Soc. 2012, 134, 20613.
  (c) Hao, W. ; Geng, W. ; Zhang, W. X. ; Xi, Z. Chem. -Eur. J. 2014, 20, 2605.
5. [5]
  Balz, G.; Schiemann, G.Ber.-Umweltbundesamt (Ger.) 1927, 60B, 1186.
6. [6]
  Brasen, W.R.; Hauser, C.R.Org.Synth.1954, 34, 58. doi: 10.15227/orgsyn.034.0058
7. [7]
8. [8]
  (a) Eds. : de Meijere, A. ; Diederich, F. ; Metal-Catalyzed CrossCoupling Reactions, Wiley-VCH, Weinheim, 2004, p. 437.
  (b) Eds. : de Meijere, A. ; Braese, S. ; Oestreich, M. Metal-Catalyzed Cross-Coupling Reactions And More, Wiley-VCH, Weinheim, 2014.
9. [9]
  Corriu, R.J.P.; Masse, J.P.J.Chem.Soc., Chem.Commun.1972, 144a.
10. [10]
  Tamao, K.; Sumitani, K.; Kumada, M.J.Am.Chem.Soc.1972, 94, 4374. doi: 10.1021/ja00767a075
11. [11]
  Terao, J.; Kambe, N.Acc.Chem.Res.2008, 41, 1545. doi: 10.1021/ar800138a
12. [12]
  Wenkert, E.; Han, A.-L.; Jenny, C.-J.J.Chem.Soc., Chem.Commun.1988, 975.
13. [13]
  (a) Wenkert, E. ; Michelotti, E. L. ; Swindell, C. S. J. Am. Chem. Soc. 1979, 101, 2246.
  (b) Yu, D. -G. ; Li, B. -J. ; Shi, Z. -J. Acc. Chem. Res. 2010, 43, 1486.
  (c) Rosen, B. M. ; Quasdorf, K. W. ; Wilson, D. A. ; Zhang, N. ; Resmerita, A. -M. ; Garg, N. K. ; Percec, V. Chem. Rev. 2011, 111, 1346.
  (d) Su, B. ; Cao, Z. -C. ; Shi, Z. -J. Acc. Chem. Res. 2015, 48, 886.
  (e) Tobisu, M. ; Chatani, N. Acc. Chem. Res. 2015, 48, 1717.
14. [14]
  (a) Clot, E. ; Eisenstein, O. ; Jasim, N. ; MacGregor, S. A. ; McGrady, J. E. ; Perutz, R. N. Acc. Chem. Res. 2011, 44, 333.
  (b) Keyes, L. ; Love, J. A. RSC Catal. Ser. 2013, 11, 159.
  (c) Yang, S. -D. In Homogeneous Transition-Metal-Catalyzed C-F Sctivation, John Wiley & Sons, New York, 2015, pp. 203~268.
15. [15]
  Reeves, J.T.; Fandrick, D.R.; Tan, Z.; Song, J.J.; Lee, H.; Yee, N.K.; Senanayake, C.H.Org.Lett.2010, 12, 4388. doi: 10.1021/ol1018739
16. [16]
  Guo, W.-J.; Wang, Z.-X.Tetrahedron 2013, 69, 9580. doi: 10.1016/j.tet.2013.09.039
17. [17]
  Guisan-Ceinos, M.; Martin-Heras, V.; Tortosa, M.J.Am.Chem.Soc.2017, 139, 8448. doi: 10.1021/jacs.7b05273
18. [18]
  Ma, S.; Liu, Q.; Tang, X.; Cai, Y.Asian J.Org.Chem.2017, 6, 1209. doi: 10.1002/ajoc.v6.9
19. [19]
  (a) Dieck, H. A. ; Heck, R. F. J. Am. Chem. Soc. 1974, 96, 1133.
  (b) Heck, R. F. Acc. Chem. Res. 1979, 12, 146.
20. [20]
  Pan, Y.; Zhang, Z.; Hu, H.Synthesis 1995, 245.
21. [21]
  (a) Miyaura, N. ; Suzuki, A. Chem. Rev. 1995, 95, 2457.
  (b) Miyaura, N. Top. Curr. Chem. 2002, 219, 11.
22. [22]
  Blakey, S.B.; MacMillan, D.W.C.J.Am.Chem.Soc.2003, 125, 6046. doi: 10.1021/ja034908b
23. [23]
  Buszek, K.R.; Brown, N.Org.Lett.2007, 9, 707. doi: 10.1021/ol063027h
24. [24]
  de la Herrán, G.; Segura, A.; Csákÿ, A.G.Org.Lett.2007, 9, 961. doi: 10.1021/ol063042m
25. [25]
  Humphrey, G.R.; Kuethe, J.T.Chem.Rev.2006, 106, 2875. doi: 10.1021/cr0505270
26. [26]
  Maity, P.; Shacklady-McAtee, D.M.; Yap, G.P.A.; Sirianni, E.R.; Watson, M.P.J.Am.Chem.Soc.2013, 135, 280. doi: 10.1021/ja3089422
27. [27]
  Shacklady-McAtee, D.M.; Roberts, K.M.; Basch, C.H.; Song, Y.G.; Watson, M.P.Tetrahedron 2014, 70, 4257. doi: 10.1016/j.tet.2014.03.039
28. [28]
  Liu, X.-Y.; Zhu, H.-B.; Shen, Y.-J.; Jiang, J.; Tu, T.Chin.Chem.Lett.2017, 28, 350. doi: 10.1016/j.cclet.2016.09.006
29. [29]
  Wang, T.; Yang, S.; Xu, S.; Han, C.; Guo, G.; Zhao, J.RSC Adv.2017, 7, 15805. doi: 10.1039/C7RA02549A
30. [30]
  Turtscher, P.L.; Davis, H.J.; Phipps, R.J.Synthesis 2018, 50, 793. doi: 10.1055/s-0036-1588548
31. [31]
  Basch, C.H.; Liao, J.; Xu, J.; Piane, J.J.; Watson, M.P.J.Am.Chem.Soc.2017, 139, 5313. doi: 10.1021/jacs.7b02389
32. [32]
  (a) Katritzky, A. R. ; Gruntz, U. ; Kenny, D. H. ; Rezende, M. C. ; Sheikh, H. J. Chem. Soc., Perkin Trans. 1 1979, 430.
  (b) Katritzky, A. R. ; Marson, C. M. Angew. Chem., Int. Ed. 1984, 23, 420.
33. [33]
  (a) Shao, Z. ; Li, X. ; Chang, H. ; Wei, W. Chemistry 2013, 76, 704.
  (b) Dilman, A. D. ; Levin, V. V. Tetrahedron Lett. 2016, 57, 3986.
34. [34]
  Xie, L.G.; Wang, Z.X.Angew.Chem., Int.Ed.2011, 50, 4901. doi: 10.1002/anie.v50.21
35. [35]
  (a) Zhang, X. -Q. ; Wang, Z. -X. J. Org. Chem. 2012, 77, 3658.
  (b) Yang, X. ; Wang, Z. -X. Organometallics 2014, 33, 5863.
36. [36]
  Wang, D.-Y.; Morimoto, K.; Yang, Z.-K.; Wang, C.; Uchiyama, M.Chem.-Asian J.2017, 12, 2554. doi: 10.1002/asia.v12.19
37. [37]
  (a) Stille, J. K. Angew. Chem., Int. Ed. 1986, 25, 508.
  (b) Fugami, K. ; Kosugi, M. Top. Curr. Chem. 2002, 219, 87.
38. [38]
  Wang, D.-Y.; Kawahata, M.; Yang, Z.-K.; Miyamoto, K.; Komagawa, S.; Yamaguchi, K.; Wang, C.; Uchiyama, M.Nat.Commun.2016, 7, 12937. doi: 10.1038/ncomms12937
39. [39]
  Yamamura, M. ; Moritani, I. ; Murahashi, S. -I. J. Organomet. Chem. 1975, 91, C39.
  (b) Murahashi, S. ; Yamamura, M. ; Yanagisawa, K. ; Mita, N. ; Kondo, K. J. Org. Chem. 1979, 44, 2408.
  (c) Giannerini, M. ; Fañanás-Mastral, M. ; Feringa, B. L. Nat. Chem. 2013, 5, 667.
40. [40]
  Yang, Z.-K.; Wang, D.-Y.; Minami, H.; Ogawa, H.; Ozaki, T.; Saito, T.; Miyamoto, K.; Wang, C.; Uchiyama, M.Chem.-Eur.J.2016, 22, 15693. doi: 10.1002/chem.201603436
41. [41]
  He, F.; Wang, Z.-X.Tetrahedron 2017, 73, 4450. doi: 10.1016/j.tet.2017.06.004
42. [42]
  Ogawa, H.; Yang, Z.-K.; Minami, H.; Kojima, K.; Saito, T.; Wang, C.; Uchiyama, M.ACS Catal.2017, 7, 3988. doi: 10.1021/acscatal.7b01058
43. [43]
  Zhu, F.; Tao, J.-L.; Wang, Z.-X.Org.Lett.2015, 17, 4926. doi: 10.1021/acs.orglett.5b02458
44. [44]
  Yu, S.; Liu, S.; Lan, Y.; Wan, B.; Li, X.J.Am.Chem.Soc.2015, 137, 1623. doi: 10.1021/ja511796h
45. [45]
  Uemura, T.; Yamaguchi, M.; Chatani, N.Angew.Chem., Int.Ed.2016, 55, 3162. doi: 10.1002/anie.201511197
46. [46]
  Klauck, F.J.R.; James, M.J.; Glorius, F.Angew.Chem., Int.Ed.2017, 56, 12336. doi: 10.1002/anie.201706896
47. [47]
  Spettel, M.; Pollice, R.; Schnürch, M.Org.Lett.2017, 19, 4287. doi: 10.1021/acs.orglett.7b01946
48. [48]
  (a) Hofmann, A. W. Justus Liebigs Ann. Chem. 1851, 79, 11.
  (b) von Hofmann, A. W. Justus Liebigs Ann. Chem. 1851, 78, 253.
49. [49]
  Li, J.W.; Zheng, Z.J.; Xiao, T.T.; Xu, P.F.; Wei, H.Asian J.Org.Chem.2018, 7, 133. doi: 10.1002/ajoc.v7.1
50. [50]
  (a) Gambarotta, S. ; Alper, H. J. Organomet. Chem. 1980, 194, C19.
  (b) Lei, Y. ; Zhang, R. ; Wu, Q. ; Mei, H. ; Xiao, B. ; Li, G. J. Mol. Catal. A 2014, 381, 120.
  (c) Lei, Y. ; Zhang, R. ; Wu, L. ; Wu, Q. ; Mei, H. ; Li, G. Appl. Organomet. Chem. 2014, 28, 310.
51. [51]
  Moragas, T.; Gaydou, M.; Martin, R.Angew.Chem., Int.Ed.2016, 55, 5053. doi: 10.1002/anie.v55.16
52. [52]
  Zhang, X.-Q.; Wang, Z.-X.Org.Bioorg.Chem.2014, 12, 1448. doi: 10.1039/c3ob41989d
53. [53]
  Zhang, H.; Hagihara, S.; Itami, K.Chem.-Eur.J.2015, 21, 16796. doi: 10.1002/chem.v21.47
54. [54]
  Hu, J.; Sun, H.; Cai, W.; Pu, X.; Zhang, Y.; Shi, Z.J.Org.Chem.2016, 81, 14. doi: 10.1021/acs.joc.5b02557
55. [55]
  Basch, C.H.; Cobb, K.M.; Watson, M.P.Org.Lett.2016, 18, 136. doi: 10.1021/acs.orglett.5b03455
56. [56]
  Mfuh, A.M.; Doyle, J.D.; Chhetri, B.; Arman, H.D.; Larionov, O.V.J.Am.Chem.Soc.2016, 138, 2985. doi: 10.1021/jacs.6b01376
57. [57]
  (a) Said, S. A. ; Fiksdahl, A. Tetrahedron: Asymmetry 2001, 12, 1947.
  (b) Gui, Y. ; Tian, S. K. Org. Lett. 2017, 19, 1554.
  (c) Erika, B. ; Istvan, G. ; Gyorgy, K. Lett. Org. Chem. 2011, 8, 22.
58. [58]
  Lu, F.L.; Chen, Z.Y.; Li, Z.; Wang, X.Y.; Peng, X.Y.; Li, C.; Li, R.; Pei, H.Q.; Wang, H.M.; Gao, M.Asian J.Org.Chem.2018, 7, 141. doi: 10.1002/ajoc.v7.1
1. [1]
  Geyang Song , Dong Xue , Gang Li . Recent Advances in Transition Metal-Catalyzed Synthesis of Anilines from Aryl Halides. University Chemistry, 2024, 39(2): 321-329. doi: 10.3866/PKU.DXHX202308030
2. [2]
  Yan Li , Xinze Wang , Xue Yao , Shouyun Yu . 基于激发态手性铜催化的烯烃E→Z异构的动力学拆分——推荐一个本科生综合化学实验. University Chemistry, 2024, 39(5): 1-10. doi: 10.3866/PKU.DXHX202309053
3. [3]
  Yanhui Guo , Li Wei , Zhonglin Wen , Chaorong Qi , Huanfeng Jiang . Recent Progress on Conversion of Carbon Dioxide into Carbamates. Acta Physico-Chimica Sinica, 2024, 40(4): 2307004-0. doi: 10.3866/PKU.WHXB202307004
4. [4]
  Lu Zhuoran , Li Shengkai , Lu Yuxuan , Wang Shuangyin , Zou Yuqin . Cleavage of C―C Bonds for Biomass Upgrading on Transition Metal Electrocatalysts. Acta Physico-Chimica Sinica, 2024, 40(4): 2306003-0. doi: 10.3866/PKU.WHXB202306003
5. [5]
  Wen WANG , Ying XU , Gang XIONG , Lixin YOU , Yaguang SUN . Pd-NHC-functionalized La-metal-organic framework for efficient Suzuki-Miyaura cross-coupling reaction. Chinese Journal of Inorganic Chemistry, 2026, 42(7): 1475-1484. doi: 10.11862/CJIC.20260025
6. [6]
  Ying Wang , Mingcheng Yang , Zhu Yin , Yingqi Wang , Jiajia Cheng . Transition metal-free poly(heptazine imide) photocatalyst for C-X bond construction from katritzky salts. Acta Physico-Chimica Sinica, 2026, 42(7): 100212-. doi: 10.1016/j.actphy.2025.100212
7. [7]
  Yan Qi , Yueqin Yu , Weisi Guo , Yongjun Liu . 过渡金属参与的有机反应案例教学与实践探索. University Chemistry, 2025, 40(6): 111-117. doi: 10.12461/PKU.DXHX202411021
8. [8]
  Ruizhi Duan , Xiaomei Wang , Panwang Zhou , Yang Liu , Can Li . The role of hydroxyl species in the alkaline hydrogen evolution reaction over transition metal surfaces. Acta Physico-Chimica Sinica, 2025, 41(9): 100111-0. doi: 10.1016/j.actphy.2025.100111
9. [9]
  Lili Jiang , Shaoyu Zheng , Xuejiao Liu , Xiaomin Xie . Copper-Catalyzed Oxidative Coupling Reactions for the Synthesis of Aryl Sulfones: A Fundamental and Exploratory Experiment for Undergraduate Teaching. University Chemistry, 2025, 40(7): 267-276. doi: 10.12461/PKU.DXHX202408004
10. [10]
  Xinwan Zhao , Yue Cao , Minjun Lei , Zhiliang Jin , Tsubaki Noritatsu . Constructing S-scheme heterojunctions by integrating covalent organic frameworks with transition metal sulfides for efficient noble-metal-free photocatalytic hydrogen evolution. Acta Physico-Chimica Sinica, 2025, 41(12): 100152-0. doi: 10.1016/j.actphy.2025.100152
11. [11]
  Yifeng TAN , Ping CAO , Kai MA , Jingtong LI , Yuheng WANG . Synthesis of pentaerythritol tetra(2-ethylthylhexoate) catalyzed by h-MoO₃/SiO₂. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2155-2162. doi: 10.11862/CJIC.20240147
12. [12]
  Guojie Xu , Fang Yu , Yunxia Wang , Meng Sun . Introduction to Metal-Catalyzed β-Carbon Elimination Reaction of Cyclopropenones. University Chemistry, 2024, 39(8): 169-173. doi: 10.3866/PKU.DXHX202401060
13. [13]
  Ruige ZHANG , Zhe ZHANG , He ZHENG , Zhan SHI . Recent advances of metal-organic frameworks for alkaline electrocatalytic oxygen evolution reaction. Chinese Journal of Inorganic Chemistry, 2025, 41(10): 2011-2028. doi: 10.11862/CJIC.20250185
14. [14]
  Pengzi Wang , Wenjing Xiao , Jiarong Chen . Copper-Catalyzed C―O Bond Formation by Kharasch-Sosnovsky-Type Reaction. University Chemistry, 2025, 40(4): 239-244. doi: 10.12461/PKU.DXHX202406090
15. [15]
  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
16. [16]
  Ju Wang , Jie Xu , Shuangshuang Li , Chunhua Du , Xianli Wu , Lihua Lu , Xinxin Zhang . Rational design and synthesis of deep eutectic solvent-derived carbon-supported transition metal electrocatalysts for nitrate reduction to ammonia. University Chemistry, 2026, 41(7): 309-318. doi: 10.12461/PKU.DXHX202505099
17. [17]
  Wenliang Wang , Weina Wang , Tian Sheng , Nan Wei , Sufan Wang , Tao Zhou . 过渡金属/氧化物催化CO₂加H₂还原生成甲醇的甲酸盐与甲酰基路径的前线轨道对称性分析. University Chemistry, 2026, 41(9): 405-411. doi: 10.12461/PKU.DXHX202508059
18. [18]
  Xiqing Liang , Tian Zhao , Jiawei Li , Haohui Tan , Hai Chen , Liyan Zeng . Pentaerythritol’s Journey of Making Friends. University Chemistry, 2025, 40(10): 175-185. doi: 10.12461/PKU.DXHX202412009
19. [19]
  Wuxin Bai , Qianqian Zhou , Zhenjie Lu , Ye Song , Yongsheng Fu . Co-Ni Bimetallic Zeolitic Imidazolate Frameworks Supported on Carbon Cloth as Free-Standing Electrode for Highly Efficient Oxygen Evolution. Acta Physico-Chimica Sinica, 2024, 40(3): 2305041-0. doi: 10.3866/PKU.WHXB202305041
20. [20]
  Kangjuan Cheng , Chunxiao Liu , Youpeng Wang , Qiu Jiang , Tingting Zheng , Xu Li , Chuan Xia . Design of noble metal catalysts and reactors for the electrosynthesis of hydrogen peroxide. Acta Physico-Chimica Sinica, 2025, 41(10): 100112-0. doi: 10.1016/j.actphy.2025.100112

Get Citation

PDF

XML

Metrics

PDF Downloads(119)
Abstract views(7752)
HTML views(1915)

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