Citation: Li Juanhua, Liu Kunming, Duan Xinfang, Liu Jinbiao. Recent Progress in Iron Catalyzed C-C Coupling Reactions[J]. Chinese Journal of Organic Chemistry, ;2017, 37(2): 314-334. doi: 10.6023/cjoc201608009 shu

Recent Progress in Iron Catalyzed C-C Coupling Reactions

a.
School of Metallurgy and Chemical Engineering, Jiangxi University of Science and Technology, Ganzhou 341000
b.
Department of Chemistry, Beijing Normal University, Beijing 100875

Corresponding author: Liu Kunming, liukunminglkm@sina.com
Received Date: 16 August 2016
Revised Date: 22 September 2016

Fund Project: the National Natural Science Foundation of China 21502075the National Natural Science Foundation of China 21372031

Figures(38)

Transition-metal-catalyzed coupling reactions play an important role in construct C-C bond. As one of the most abundant metal in the earth's crust, along with its inexpensive price, relatively low toxicity and multiple redox states, Fe is an ideal catalyst for coupling reactions. Recently, green, highly effective and selective reactions have attracted much attention, which accelerated the research of iron catalyzed coupling. Particularly, many new catalyst systems and various reaction types such as iron catalyzed oxidative coupling, reductive coupling and C-H direct functionalization were explored during the past decade. The present review surveys the recent progress in Fe catalyzed C-C coupling concerning their reaction types, including mechanism and application. Furthermore, the prospects of this reaction are also discussed.
- iron catalyzed,
- C-C coupling reaction,
- organic synthesis
1. [1]
  (a) De Mejiere, A.; Diederich, F. Metal-Catalyzed Cross-Coupling Reactions, Wiley-VCH, Weinheim, 2004.
  (b) Hartwig, J. F. Organotransition Metal Chemistry, University Science Books, Sausalito, California, 2010.
  (c) Liu, C.; Zhang, H.; Shi, W.; Lei, A. W. Chem. Rev. 2011, 111, 1780.
2. [2]
  (a) Graening, T.; Schmalz, H.-G. Angew. Chem., Int. Ed. 2003, 42, 2580.
  (b) Nicolaou, K. C.; Bulger, P. G.; Sarlah, D. Angew. Chem., Int. Ed. 2005, 44, 4490.
  (c) Magano, J.; Dunetz, J. R. Chem. Rev. 2011, 111, 2177.
3. [3]
  (a) Wu, X.-F.; Anbarasan, P.; Neumann, H.; Beller, M. Angew. Chem., Int. Ed. 2010, 49, 9047.
  (b) Chen, X.; Engle, K. M.; Wang, D.-H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2009, 48, 5094.
4. [4]
  Van Leeuwen, P. N. M.; Kamer, P. C. J.; Claver, C.; Pamies, O.; Dieguez, M. Chem. Rev. 2011, 111, 2077. doi: 10.1021/cr1002497
5. [5]
6. [6]
7. [7]
  (a) Bolm, C.; Legros, J.; Le Paih, J.; Zani, L. Chem. Rev. 2004, 104, 6217.
  (b) Plietker, B. Iron Catalysis in Organic Chemistry: Reactions and Applications, Wiley-VCH, Weinheim, 2008.
  (c) Sherry, B. D.; Fürstner, A. Acc. Chem. Res. 2008, 41, 1500.
  (d) Fürstner, A. Angew. Chem., Int. Ed. 2009, 48, 1364.
  (e) Cahiez, G.; Moyeux, A. Chem. Rev. 2010, 110, 1435.
8. [8]
9. [9]
  Kharasch, M. S.; Fields, E. K. J. Am. Chem. Soc. 1941, 63, 2316. doi: 10.1021/ja01854a006
10. [10]
  (a) Kochi, J. K. J. Am. Chem. Soc. 1971, 93, 1487.
  (b) Kochi, J. K. J. Org. Chem. 1976, 41, 599.
11. [11]
  Walborsky, H. M. J. Org. Chem. 1981, 46, 5074. doi: 10.1021/jo00338a004
12. [12]
  Molander, G. A. Tetrahedron Lett. 1983, 24, 5449. doi: 10.1016/S0040-4039(00)94109-1
13. [13]
  (a) Cahiez, G. Synthesis 1998, 1199.
  (b) Cahiez, G. Synlett 2001, 1901.
  (c) Cahiez, G.; Avedissian, H. Tetrahedron Lett. 1998, 39, 6159.
  (d) Cahiez, G.; Marquais, S. Pure Appl. Chem. 1996, 68, 53.
14. [14]
  (a) Fürstner, A.; Leitner, A. Angew. Chem., Int. Ed. 2002, 41, 609.
  (b) Fürstner, A.; Leitner, A.; Méndez, M.; Krause, H. J. Am. Chem. Soc. 2002, 124, 13856.
15. [15]
  (a) Fürstner, A.; Leitner, A. Angew. Chem., Int. Ed. 2003, 42, 308.
  (b) Fürstner, A.; Souza, D. D.; Rapado, L. P.; Jensen, J. T. Angew. Chem., Int. Ed. 2003, 42, 5358.
  (c) Fürstner, A.; Turet, L. Angew. Chem., Int. Ed. 2005, 44, 3462.
16. [16]
  Scheiper, B.; Bonnekessel, M.; Krause, H.; Fürstner, A. J. Org. Chem. 2004, 69, 3949.
17. [17]
  Seidel, G.; Laurich, D.; Fürstner, A. J. Org. Chem. 2004, 69, 3950. doi: 10.1021/jo049885d
18. [18]
  (a) Jonas, K.; Schieferstein, L.; KrMger, C.; Tsay, Y.-H. Angew. Chem., Int. Ed. Engl. 1979, 18, 550.
  (b) Jonas, K.; Schieferstein, L. Angew. Chem., Int. Ed. Engl. 1979, 18, 549.
19. [19]
  Hocek, M.; Dvořákova, H. J. Org. Chem. 2003, 68, 5773. doi: 10.1021/jo034351i
20. [20]
  Ottesen, L. K.; Fredrik, E. K.; Olsson, R. Org. Lett. 2006, 8, 1771. doi: 10.1021/ol0600234
21. [21]
  Nakamura, M.; Matsuo, K.; Ito, S.; Nakamura, E. J. Am. Chem. Soc. 2004, 126, 3686. doi: 10.1021/ja049744t
22. [22]
  Martin, R.; Fürstner, A. Angew. Chem., Int. Ed. 2004, 43, 3955. doi: 10.1002/(ISSN)1521-3773
23. [23]
  Cahiez, G.; Habiak, V.; Duplais, C.; Moyeux, A. Angew. Chem., Int. Ed. 2007, 46, 4364. doi: 10.1002/(ISSN)1521-3773
24. [24]
  Cahiez, G.; Duplais, C.; Moyeux, A. Org. Lett. 2007, 9. 325.
25. [25]
  Gurinot, A.; Reymond, S.; Cossy, J. Angew. Chem., Int. Ed. 2007, 46, 6521. doi: 10.1002/(ISSN)1521-3773
26. [26]
  Gurinot, A.; Lepesqueux, G.; Sable, S.; Reymond, S.; Cossy, J. J. Org. Chem. 2010, 75, 5151. doi: 10.1021/jo100871m
27. [27]
  (a) Bedford, R. B.; Bruce, D. W.; Frost, R. M.; Goodbyb, J. W.; Hirdb, M. Chem. Commun. 2004, 2822.
  (b) Bedford, R. B.; Bruce, D. W.; Frost, R. M.; Hirdb, M. Chem. Commun. 2005, 4161.
28. [28]
  Chowdhury, R. R.; Crane, A. K.; Fowler, C.; Kwong, P.; Kozak, C. M. Chem. Commun. 2008, 94.
29. [29]
  Yamaguchi, Y.; Ando, H.; Nagaya, M.; Hinago, H.; Ito, T.; Asami, M. Chem. Lett. 2011, 40, 983. doi: 10.1246/cl.2011.983
30. [30]
  Bedford, R. B.; Betham, M.; Bruce, D. W.; Danopoulos, A. A.; Robert, M. F.; Michael, H. J. Org. Chem. 2006, 71, 1104. doi: 10.1021/jo052250+
31. [31]
  Bedford, R. B.; Huwea, M.; Wilkinson, M. C. Chem. Commun. 2009, 600.
32. [32]
  Hatakeyama, T.; Kondo, Y.; Fujiwara, Y.-I.; Takaya, H.; Ito, S.; Nakamura, E.; Nakamura, M. Chem. Commun. 2009, 1216.
33. [33]
  (a) Tamura, M.; Kochi, J. J. Organomet. Chem. 1971, 31, 289.
  (b) Tamura, M.; Kochi, J. K. Bull. Chem. Soc. Jpn. 1971, 44, 3063.
34. [34]
  Adams, C. J.; Bedford, R. B.; Carter, E.; Gower, N. J.; Haddow, M. F.; Harvey, J. N.; Huwe, M.; Cartes, M. Á.; Mansell, S. M.; Mendoza, C.; Murphy, D. M.; Neeve, E. C.; Nunn, J. J. Am. Chem. Soc. 2012, 134, 10333. doi: 10.1021/ja303250t
35. [35]
  Bedford, R. B.; Carter, E.; Cogswell, P. M.; Gower, N. J.; Haddow, M. F.; Harvey, J. N.; Murphy, D. M.; Neeve, E. C.; Nunn, J. Angew. Chem., Int. Ed. 2013, 52, 1285. doi: 10.1002/anie.201207868
36. [36]
  Jana, R.; Pathak, T. P.; Sigman, M. S. Chem. Rev. 2012, 111, 1417.
37. [37]
  (a) Hatakeyama, T.; Hashimoto, T.; Kondo, Y.; Fujiwara, Y.; Seike, H.; Takaya, H.; Tamada, Y.; Ono, T.; Nakamura, M. J. Am. Chem. Soc. 2010, 132, 10674.
  (b) Hashimoto, T.; Hatakeyama, T.; Nakamura, M. J. Org. Chem. 2012, 77, 1168.
  (c) Hatakeyama, T.; Hashimoto, T.; Kathriarachchi, K. K. A. D. S.; Zenmyo, T.; Seike, H.; Nakamura, M. Angew. Chem., Int. Ed. 2012, 124, 1.
  (d) Nakagawa, N.; Hatakeyama, T.; Nakamura, M. Chem. Lett. 2015, 44, 486.
38. [38]
  Bedford, R. B.; Brenner, P. B.; Carter, E.; Clifton, J.; Cogswell, P. M.; Gower, N. J.; Haddow, M. F.; Harvey, J. N.; Kehl, J. A.; Murphy, D. M.; Neeve, E. C.; Neidig, M. L.; Nunn, J.; Snyder, B. E. R.; Taylor, J. Organometallics 2014, 33, 5767. doi: 10.1021/om500518r
39. [39]
  Nakamura, M.; Hirai, A.; Nakamura, E. J. Am. Chem. Soc. 2000, 122, 978. doi: 10.1021/ja983066r
40. [40]
  Jin, M.; Adak, L.; Nakamura, M. J. Am. Chem. Soc. 2015, 137, 7128. doi: 10.1021/jacs.5b02277
41. [41]
  Jin, M.; Nakamura, M. Chem. Lett. 2011, 40, 1012. doi: 10.1246/cl.2011.1012
42. [42]
  Cahiez, G.; Marquais, S. Pure Appl. Chem. 1996, 68, 53..
43. [43]
  (a) Sapountzis, I.; Lin, W. W.; Kofink, C. C.; Despotopoulou, C.; Knochel, P. Angew. Chem., Int. Ed. 2005, 44, 1654.
  (b) Kofink, C. C.; Blank, B.; Pagano, S.; Gótz, N.; Knochel, P. Chem. Commun. 2007, 1954.
44. [44]
  (a) Hatakeyama, T.; Nakagawa, N.; Nakamura, M. Org. Lett. 2009, 11, 4496.
  (b) Ito, S.; Fujiwara, Y.-I.; Nakamura, E.; Nakamura, M. Org. Lett. 2009, 11, 4306.
45. [45]
  Cahiez, G.; Habiak, V.; Gager, O. Org. Lett. 2008, 10, 2389. doi: 10.1021/ol800816f
46. [46]
  Li, B.-J.; Xu, L.; Wu, Z.-H.; Guan, B.-T.; Sun, C.-L.; Wang, B.-Q.; Shi, Z.-J. J. Am. Chem. Soc. 2009, 131, 14656. doi: 10.1021/ja907281f
47. [47]
  Agrawal, T.; Cook, S. P. Org. Lett. 2013, 15, 96. doi: 10.1021/ol303130j
48. [48]
  Itami, K.; Higashi, S.; Mineno, M.; Yoshida, J.-I. Org. Lett. 2005, 7, 1219. doi: 10.1021/ol047504c
49. [49]
  Denmark, S. E.; Cresswell, A. J. J. Org. Chem. 2013, 78, 12593. doi: 10.1021/jo402246h
50. [50]
  Chandra, M.; Volla, R.; Vogel, P. Angew. Chem., Int. Ed. 2008, 47, 1305. doi: 10.1002/(ISSN)1521-3773
51. [51]
  Dongol, K. G.; Koh, H.; Sau, M. and Chai, C. L. L. Adv. Synth. Catal. 2007, 349, 1015. doi: 10.1002/(ISSN)1615-4169
52. [52]
  Hatakeyama, T.; Hashimoto, T.; Kathriarachchi, K. K. A. D. S.; Zenmyo, T.; Seike, H.; Nakamura, M. Angew. Chem., Int. Ed. 2012, 51, 8834. doi: 10.1002/anie.v51.35
53. [53]
  Hatakeyama, T.; Yoshimoto, Y.; Gabriel, T.; Nakamura, M. Org. Lett. 2008, 10, 5341. doi: 10.1021/ol8020226
54. [54]
  Xie, X.; Xu, X. B.; Li, H. F.; Xu, X. L.; Yang, J. Y.; Lia, Y. Z. Adv. Synth. Catal. 2009, 351, 1263. doi: 10.1002/adsc.v351:9
55. [55]
  Carril, M.; Correa, A.; Bolm, C. Angew. Chem., Int. Ed. 2008, 47, 4862. doi: 10.1002/(ISSN)1521-3773
56. [56]
  Mao, J. C.; Xie, G. L.; Wu, M. Y.; Guo, J.; Ji, S. J. Adv. Synth. Catal. 2008, 350, 2477. doi: 10.1002/adsc.v350:16
57. [57]
  Chandra, M.; Volla, R.; Vogel, P. Tetrahedron Lett. 2008, 49, 5961. doi: 10.1016/j.tetlet.2008.07.151
58. [58]
  Hatakeyama, T.; Okada, Y.; Yoshimoto, Y.; Nakamura M. Angew. Chem., Int. Ed. 2011, 50, 10973. doi: 10.1002/anie.v50.46
59. [59]
  Nakagawa, N.; Hatakeyama, T.; Nakamura, M. Chem. Lett. 2015, 44, 486. doi: 10.1246/cl.141167
60. [60]
  Cheung, C. W.; Ren, P.; Hu, X. L. Org. Lett. 2014, 16, 2566. doi: 10.1021/ol501087m
61. [61]
  Quintin, J.; Franck, X.; Hocquemiller, R.; Figadère, B. Tetrahe-dron Lett. 2002, 43, 3547. doi: 10.1016/S0040-4039(02)00568-3
62. [62]
  Ludovic, B.; Mirca, D.; Alain, T.; Nelly, P. J. Heterocycl. Chem. 2005, 42, 1423. doi: 10.1002/jhet.v42:7
63. [63]
  Kuzmina, O. M.; Steib, A. K.; Flubacher, D.; Knochel, P. Org. Lett. 2012, 14, 4818. doi: 10.1021/ol302136c
64. [64]
  Kuzmina, O. M.; Steib, A. K.; Markiewicz, J. T.; Flubacher, D.; Knochel, P. Angew. Chem., Int. Ed. 2013, 52, 4945. doi: 10.1002/anie.v52.18
65. [65]
  Hatakeyama, T.; Nakamura, M. J. Am. Chem. Soc. 2007, 129, 9844. doi: 10.1021/ja073084l
66. [66]
  Hatakeyama, T.; Hashimoto, S.; Ishizuka, K.; Nakamura, M. J. Am. Chem. Soc. 2009, 131, 11949. doi: 10.1021/ja9039289
67. [67]
  Agrawal, T.; Cook, S. P. Org. Lett. 2014, 16, 5080. doi: 10.1021/ol5024344
68. [68]
  (a) Liu, C.; Zhang, H.; Shi, W.; Lei, A. W. Chem. Rev. 2011, 1780.
  (b) Shi, W.; Liu, C.; Lei, A. W. Chem. Soc. Rev. 2011, 40, 2761.
69. [69]
  Selected reviews:
  (a) Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 4176.
  (b) Fu, G. C. Acc. Chem. Res. 2008, 41, 1555.
  (c) Martin, R.; Buchwald, S. L. Acc. Chem. Res. 2008, 41, 1461.
  (d) Marion, N.; Nolan, S. P. Acc. Chem. Res. 2008, 41, 1440.
  (e) Fortman, G. C.; Nolan, S. P. Chem. Soc. Rev. 2011, 40, 5151.
70. [70]
  Selected reviews:
  (a) Mulvey, R. E.; Mongin, F.; Uchiyama, M.; Kondo, Y. Angew. Chem., Int. Ed. 2007, 46, 3802.
  (b) Haag, B.; Mosrin, M.; Ila, H.; Malakhov, V.; Knochel, P. Angew. Chem., Int. Ed. 2011, 50, 9794.
  (c) Mongin, F.; Harrison-Marchand, A. Chem. Rev. 2013, 113, 7563.
  (d) Klatt, T.; Markiewicz, J. T. Sämann, C.; Knochel, P. J. Org. Chem. 2014, 79, 4253.
71. [71]
  Nagano, T.; Hayashi, T. Org. Lett. 2005, 7, 491. doi: 10.1021/ol047509+
72. [72]
  Cahiez, G.; Chaboche, C.; Betzer, F. M.; Ahr, M. Org. Lett. 2005, 7, 1943. doi: 10.1021/ol050340v
73. [73]
  Cahiez, G.; Moyeux, A.; Buendia, J.; Duplais, C. J. Am. Chem. Soc. 2007, 129, 13788. doi: 10.1021/ja075417k
74. [74]
  Liu, W.; Lei, A. W. Tetrahedron Lett. 2008, 49, 610. doi: 10.1016/j.tetlet.2007.11.144
75. [75]
  Truong, T.; Alvarado, J.; Tran, L. D.; Daugulis, O. Org. Lett. 2010, 12, 1200. doi: 10.1021/ol902970z
76. [76]
  Cahiez, G.; Foulgoc, L.; Moyeux, A. Angew. Chem., Int. Ed. 2009, 48, 2969. doi: 10.1002/anie.200900175
77. [77]
  Liu, K. M.; Liao, L. Y.; Duan, X. F. Chem. Commun. 2015, 51, 1124. doi: 10.1039/C4CC08494B
78. [78]
  Liu, K. M.; Wei, J.; Duan, X. F. Chem. Commun. 2015, 51, 4655. doi: 10.1039/C5CC00514K
79. [79]
  Xu, X. L.; Cheng, D. P.; Pei, W. J. Org. Chem. 2006, 71, 6637. doi: 10.1021/jo060673l
80. [80]
  Sridevi, V. S.; Leong, W. -K. Tetrahedron Lett. 2007, 48, 6669. doi: 10.1016/j.tetlet.2007.07.120
81. [81]
  Czaplik, W. M.; Mayer, M.; von Wangelin, A. J. ChemCatChem 2011, 3, 135 doi: 10.1002/cctc.201000276
82. [82]
  For selected literatues on Pd catalyzed C-H activation:
  (a) Jia, C.; Piao, D.; Oyamada, J.; Lu, W.; Kitamura, T.; Fujiwara, Y. Science 2000, 287, 1992.
  (b) Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147.
  (c) Chen, X.; Engle, K. M.; Wang, D.-H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2009, 48, 5094.
  Ir catalyzed C-H activation:
  (d) Cho, J.-Y.; Tse, M. K.; Holmes, D. R.; Maleczka, E., Jr.; Smith, M. R., Ⅲ Science 2002, 295, 305.
  (e) Mkhalid, I. A. I.; Barnard, J. H.; Marder, T. B.; Murphy, J. M.; Hartwig, J. F. Chem. Rev. 2010, 110, 890.
  Ru catalyzed C-H activation:
  (f) Ritleng, V.; Sirlin, C.; Pfeffer, M. Chem. Rev. 2002, 102, 1731.
  (g) Colby, D. A.; Bergman, R. G.; Ellman, J. A. Chem. Rev. 2010, 110, 624. Pt catalyzed C-H activation:
  (h) Lersch, M.; Tilset, M. Chem. Rev. 2005, 105, 2471.
  (i) Yang, S.; Li, Z.; Jian, X.; He, C. Angew. Chem., Int. Ed. 2009, 48, 3999.
83. [83]
  Jones, W. D.; Foster, G. P.; Putinas, J. M. J. Am. Chem. Soc. 1987, 109, 5047. doi: 10.1021/ja00250a060
84. [84]
  Wen, J.; Zhang, J.; Chen, S.-Y.; Li, J.; Yu, X.-Q. Angew. Chem., Int. Ed. 2008, 47, 8897. doi: 10.1002/anie.v47:46
85. [85]
  Wen, J.; Qin, S.; Ma, L.-F.; Dong, L.; Zhang, J.; Liu, S.-S.; Duan, Y.-S.; Chen, S.-Y.; Hu, C.-W.; Yu X.-Q. Org. Lett. 2010, 12, 2694. doi: 10.1021/ol100838m
86. [86]
  Deb, A.; Manna, S.; Maji, A.; Dutta, U.; Maiti, D. Eur. J. Org. Chem. 2013, 5251.
87. [87]
  Liu, W.; Cao, H.; Lei, A. W. Angew. Chem., Int. Ed. 2010, 49, 2004. doi: 10.1002/anie.200906870
88. [88]
  Vallée, F.; Mousseau, J. J.; Charette, A. J. Am. Chem. Soc. 2010, 132, 1514. doi: 10.1021/ja910687u
89. [89]
  Norinder, J.; Matsumoto, A.; Yoshikai, N.; Nakamura, E. J. Am. Chem. Soc. 2008, 130, 5858. doi: 10.1021/ja800818b
90. [90]
  Yoshikai, N.; Matsumoto, A.; Norinder, J.; Nakamura, E. Angew. Chem., Int. Ed. 2009, 48, 2925. doi: 10.1002/anie.200900454
91. [91]
  Yoshikai, N.; Matsumoto, A.; Norinder, J.; Nakamura, E. Synlett 2010, 313.
92. [92]
  Yoshikai, N.; Asako, S.; Yamakawa, T.; Ilies, L.; Nakamura, E. Chem. Asian J. 2011, 6, 3059. doi: 10.1002/asia.v6.11
93. [93]
  Ilies, L.; Kobayashi, M.; Matsumoto, A.; Yoshikai, N.; Nakamura, E. Adv. Synth. Catal. 2012, 354, 593. doi: 10.1002/adsc.201100791
94. [94]
  Shang, R.; Ilies, L.; Matsumoto, A.; Nakamura, E. J. Am. Chem. Soc. 2013, 135, 6030. doi: 10.1021/ja402806f
95. [95]
  Shang, R.; Ilies, L.; Nakamura, E. J. Am. Chem. Soc. 2015, 137, 7660. doi: 10.1021/jacs.5b04818
96. [96]
  Shang, R.; Ilies, L.; Nakamura, E. J. Am. Chem. Soc. 2016, 138, 10132. doi: 10.1021/jacs.6b06908
97. [97]
  Li, Z. P.; Cao, L.; Li, C.-J. Angew. Chem., Int. Ed. 2007, 46, 6505. doi: 10.1002/(ISSN)1521-3773
98. [98]
  Li, Y.-Z; . Li, B.-J.; Lu, X.-Y.; Lin, S.; Shi, Z.-J. Angew. Chem., Int. Ed. 2009, 48, 1. doi: 10.1002/anie.200890275
99. [99]
  Zhang, Y.; Li, C.-J. Eur. J. Org. Chem. 2007, 4654.
100. [100]
  Li, Z. P.; Yu, R.; Li, H. J. Angew. Chem., Int. Ed. 2008, 47, 7497. doi: 10.1002/anie.v47:39
101. [101]
  Li, H.; He, Z.; Guo, X.; Li, W.; Zhao, X.; Li, Z. Org. Lett. 2009, 11, 4176. doi: 10.1021/ol901751c
102. [102]
  Liu, P.; Wang, Z. M.; Lin, J.; Hu, X. M. Eur. J. Org. Chem. 2012, 1583.
103. [103]
  For Selected literatures on the synthesis of amino acid derivatives:
  (a) Beak, P.; Zajdel, W. J.; Reitz, D. B. Chem. Rev. 1984, 84, 471.
  (b) Knowles, H. S.; Hunt, K.; Parsons, A. F. Tetrahedron Lett. 2000, 41, 7121.
  (c) Burger, K.; Geith, K.; Gaa, K. Angew. Chem., Int. Ed. Engl. 1988, 27, 848.
  (d) Ireland, R. E.; Mueller, R. H. Willard, A. K. J. Am. Chem. Soc. 1976, 98, 2868;
104. [104]
  Yoshikai, N.; Mieczkowski, A.; Matsumoto, A.; Ilies, L.; Nakamura, E. J. Am. Chem. Soc. 2010, 132, 5568. doi: 10.1021/ja100651t
105. [105]
  Qian, B.; Xie, P.; Xie, Y. J.; Huang, H. M. Org. Lett. 2011, 13, 2580. doi: 10.1021/ol200684b
106. [106]
  Volla, C. M. R.; Vogel, P. Org. Lett. 2009, 11, 1701. doi: 10.1021/ol9002509
107. [107]
  Chandrasekharam, M.; Chiranjeevi, B. P.; Gupta, K. S. V.; Sridhar, B. J. Org. Chem. 2011, 76, 10229. doi: 10.1021/jo202152b
108. [108]
  Guo, X.; Yu, R.; Li, H.; Li, Z. J. Am. Chem. Soc. 2009, 131, 17387. doi: 10.1021/ja907568j
109. [109]
  For recent reviews, see:
  (a) Davies, H. M. L.; Manning, J. R. Nature 2008, 451, 417.
  (b) Giri, R.; Shi, B. F.; Engle, K. M.; Maugel, N.; Yu, J.-Q. Chem. Soc. Rev. 2009, 38, 3242.
  (c) Doyle, M. P.; Duffy, R.; Ratnikov, M.; Zhou, L. Chem. Rev. 2010, 110, 704.
110. [110]
  Zhu, S.-F.; Zhou, Q.-L. Natl. Sci. Rev. 2014, 1, 580. doi: 10.1093/nsr/nwu019
111. [111]
  Li, Y.; Huang, J.-S.; Zhou, Z.-Y.; Che, C.-M.; You, X.-Z. J. Am. Chem. Soc. 2002, 124, 13185. doi: 10.1021/ja020391c
112. [112]
  Mbuvi, H. M.; Woo, L. K. Organometallics 2008, 27, 637. doi: 10.1021/om7007502
113. [113]
  Cai, Y.; Zhou, S.-F.; Wang, G.-P.; Zhou, Q.-L. Adv. Synth. Catal. 2011, 353, 2939. doi: 10.1002/adsc.v353.16
114. [114]
  Yang, J.-M.; Cai, Y.; Zhu, S.-F.; Zhou, Q.-L. Org. Biomol. Chem. 2016, 14, 5516. doi: 10.1039/C5OB02418H
1. [1]
  Yongjian Zhang , Fangling Gao , Hong Yan , Keyin Ye . Electrochemical Transformation of Organosulfur Compounds. University Chemistry, 2025, 40(5): 311-317. doi: 10.12461/PKU.DXHX202407035
2. [2]
  Shiyan Cheng , Yonghong Ruan , Lei Gong , Yumei Lin . Research Advances in Friedel-Crafts Alkylation Reaction. University Chemistry, 2024, 39(10): 408-415. doi: 10.12461/PKU.DXHX202403024
3. [3]
  Aidang Lu , Yunting Liu , Yanjun Jiang . Comprehensive Organic Chemistry Experiment: Synthesis and Characterization of Triazolopyrimidine Compounds. University Chemistry, 2024, 39(8): 241-246. doi: 10.3866/PKU.DXHX202401029
4. [4]
  Shuhui Li , Rongxiuyuan Huang , Yingming Pan . Electrochemical Synthesis of 2,5-Diphenyl-1,3,4-Oxadiazole: A Recommended Comprehensive Organic Chemistry Experiment. University Chemistry, 2025, 40(5): 357-365. doi: 10.12461/PKU.DXHX202407028
5. [5]
  Xuejie Wang , Guoqing Cui , Congkai Wang , Yang Yang , Guiyuan Jiang , Chunming Xu . 碳基催化剂催化有机液体氢载体脱氢研究进展. Acta Physico-Chimica Sinica, 2025, 41(5): 100044-. doi: 10.1016/j.actphy.2024.100044
6. [6]
  Yuanpei ZHANG , Jiahong WANG , Jinming HUANG , Zhi HU . Preparation of magnetic mesoporous carbon loaded nano zero-valent iron for removal of Cr(Ⅲ) organic complexes from high-salt wastewater. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1731-1742. doi: 10.11862/CJIC.20240077
7. [7]
  Jiajie Li , Xiaocong Ma , Jufang Zheng , Qiang Wan , Xiaoshun Zhou , Yahao Wang . Recent Advances in In-Situ Raman Spectroscopy for Investigating Electrocatalytic Organic Reaction Mechanisms. University Chemistry, 2025, 40(4): 261-276. doi: 10.12461/PKU.DXHX202406117
8. [8]
  Lewang Yuan , Yaoyao Peng , Zong-Jie Guan , Yu Fang . 二维共价有机框架作为光催化剂在有机合成中的研究进展. Acta Physico-Chimica Sinica, 2025, 41(8): 100086-. doi: 10.1016/j.actphy.2025.100086
9. [9]
  Xinxin YU , Yongxing LIU , Xiaohong YI , Miao CHANG , Fei WANG , Peng WANG , Chongchen WANG . Photocatalytic peroxydisulfate activation for degrading organic pollutants over the zero-valent iron recovered from subway tunnels. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 864-876. doi: 10.11862/CJIC.20240438
10. [10]
  Li'na ZHONG , Jingling CHEN , Qinghua ZHAO . Synthesis of multi-responsive carbon quantum dots from green carbon sources for detection of iron ions and L-ascorbic acid. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 709-718. doi: 10.11862/CJIC.20240280
11. [11]
  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
12. [12]
  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
13. [13]
  Zelong LIANG , Shijia QIN , Pengfei GUO , Hang XU , Bin ZHAO . Synthesis and electrocatalytic CO₂ reduction performance of metal-organic framework catalysts loaded with silver particles. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 165-173. doi: 10.11862/CJIC.20240409
14. [14]
  Dan Liu . 可见光-有机小分子协同催化的不对称自由基反应研究进展. University Chemistry, 2025, 40(6): 118-128. doi: 10.12461/PKU.DXHX202408101
15. [15]
  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
16. [16]
  Wenxiu Yang , Jinfeng Zhang , Quanlong Xu , Yun Yang , Lijie Zhang . Bimetallic AuCu Alloy Decorated Covalent Organic Frameworks for Efficient Photocatalytic Hydrogen Production. Acta Physico-Chimica Sinica, 2024, 40(10): 2312014-. doi: 10.3866/PKU.WHXB202312014
17. [17]
  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
18. [18]
  .
  CCS Chemistry 综述推荐│绿色氧化新思路：光/电催化助力有机物高效升级
  . CCS Chemistry, 2025, 7(10.31635/ccschem.024.202405369): -.
19. [19]
  Linjie ZHU , Xufeng LIU . Synthesis, characterization and electrocatalytic hydrogen evolution of two di-iron complexes containing a phosphine ligand with a pendant amine. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 939-947. doi: 10.11862/CJIC.20240416
20. [20]
  Jiaming Xu , Yu Xiang , Weisheng Lin , Zhiwei Miao . Research Progress in the Synthesis of Cyclic Organic Compounds Using Bimetallic Relay Catalytic Strategies. University Chemistry, 2024, 39(3): 239-257. doi: 10.3866/PKU.DXHX202309093

Get Citation

PDF

XML

Metrics

PDF Downloads(71)
Abstract views(3450)
HTML views(939)

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