Citation: Sun Fengli, Liu Xuemin, Chen Xinzhi, Qian Chao, Ge Xin. Progress in the Formation of C-S Bond[J]. Chinese Journal of Organic Chemistry, ;2017, 37(9): 2211-2220. doi: 10.6023/cjoc201703038 shu

Progress in the Formation of C-S Bond

Sun Fengli ^a ,
Liu Xuemin ^a ,
Chen Xinzhi ^b ,
Qian Chao ^b ,
Ge Xin ^a,b,,

a.
School of Chemical and Material Engineering, Jiangnan University, Wuxi 214122
b.
Key Laboratory of Biomass Chemical Engineering of Ministry of Education, Zhejiang University, Hangzhou 310027

Corresponding author: Ge Xin, gexin@jiangnan.edu.cn
Received Date: 22 March 2017
Revised Date: 7 May 2017
Available Online: 24 September 2017
Fund Project: the National Natural Science Foundation of China 21476194the National Natural Science Foundation of China 21606104the Project Funded by China Postdoctoral Science Foundation 2016M590536the Fundamental Research Funds for the Central Universities JUSRP115A05Project supported by the National Natural Science Foundation of China (Nos. 21476194, 21606104), the Project Funded by China Postdoctoral Science Foundation (No. 2016M590536) and the Fundamental Research Funds for the Central Universities (No. JUSRP115A05)

Figures(5)

The construction of C-S bond is the fundamental of organic synthesis, which plays an important role in the synthesis of natural products, biomolecules and functional materials. Thus, it has been received much attention. Base on the different C-S bonding method, the C-H bond activation, decarboxylation coupling reaction and Ullmann reaction are introduced. The ligands of Ullmann C-S coupling are also summarized.
- Ullmann reaction,
- C-S bond,
- coupling reaction
1. [1]
  Liu, J.; Yang, J.; Yang, Q.-H.; Wang, G.; Li, Y. Adv. Funct. Mater. 2010, 15, 1297.
2. [2]
  Dondoni, A. Angew. Chem. 2010, 120, 9133.
3. [3]
  Natarajan, A.; Guo, Y.-H.; Harbinski, F.; Fan, Y.-H.; Chen, H.; Luus, L.; Diercks, J.; Aktas, H.; Chorev, M.; Halperin, J. A. J. Med. Chem. 2004, 47, 4979. doi: 10.1021/jm0496234
4. [4]
  Cole, D. C.; Lennox, W. J.; Lombardi, S.; Ellingboe, J. W.; Bernotas, R. C.; Tawa, G. J.; Mazandarani, H.; Smith, D. L.; Zhang, G.-M.; Coupet, J.; Schechter, L. E. J. Med. Chem. 2005, 48, 353. doi: 10.1021/jm049243i
5. [5]
  Banerjee, M.; Poddar, A.; Mitra, G.; Surolia, A.; Owa, T.; Bhattacharyya, B. J. Med. Chem. 2005, 48, 547. doi: 10.1021/jm0494974
6. [6]
  Wang, Y.-F.; Zeng, J.-H.; Cui, X.-R. Chin. J. Org. Chem. 2010, 30, 181(in Chinese).
7. [7]
  Cheng, Y.-J.; Sun, L.-P. Chin. J. Org. Chem. 2013, 33, 877(in Chinese).
8. [8]
  Deng, W.; Liu, L.; Guo, Q.-X. Chin. J. Org. Chem. 2004, 24, 150(in Chinese). doi: 10.3321/j.issn:0253-2786.2004.02.004
9. [9]
  Kariya, A.; Yamaguchi, T.; Nobuta, T.; Tada, N.; Miura, T.; Itoh, A. RSC Adv. 2014, 4, 13191. doi: 10.1039/C3RA47863G
10. [10]
  Gurbuz, N.; Karaca, E. O.; Ozdemir, I.; Cetinkaya, B. Chem. Ber. 1901, 34, 2174. doi: 10.1002/(ISSN)1099-0682
11. [11]
  Zhu, F.; Wang, Z.-X. Org. Lett. 2015, 17, 1601. doi: 10.1021/acs.orglett.5b00510
12. [12]
  Li, J.; Huang, H.-N.; Liang, W.-H.; Gao, Q.; Duan, Z. Org. Lett. 2012, 15, 282.
13. [13]
  Zhu, J.-Y.; Chen, Y.; Lin, F.; Wang, B.-S.; Chen, Z.-W.; Liu, L.-X. Org. Biomol. Chem. 2015, 13, 3711. doi: 10.1039/C4OB02586E
14. [14]
  Varun, B. V.; Prabhu, K. R. J. Org. Chem. 2014, 79, 9655. doi: 10.1021/jo501793q
15. [15]
  Hostier, T.; Ferey, V.; Ricci, G.; Pardoa, D. G.; Cossy, J. Chem. Commun. 2015, 51, 13898. doi: 10.1039/C5CC05421D
16. [16]
  Yu, J.-Q.; Ding, K.-L. Acta Chim. Sinica 2015, 73, 1223(in Chinese).
17. [17]
  Su, Y.; Zhou, X.-J.; He, C.-L.; Zhang, W.; Ling, X.; Xiao, X. J. Org. Chem. 2016, 81, 4981. doi: 10.1021/acs.joc.6b00475
18. [18]
  Suzuki, H.; Abe, H. Synth. Commun. 1996, 26, 3413. doi: 10.1080/00397919608003745
19. [19]
  Li, H.-L.; Wang, Z.-L.; Deng, W.-P. Chin. J. Org. Chem. 2016, 36, 2419(in Chinese).
20. [20]
  Yang, D.-S.; Yan, K.-L.; Wei, W.; Li, G.-Q.; Lu, S.-L.; Zhao, C.-X.; Tian, L.-J.; Wang, H. J. Org. Chem. 2015, 80, 11073. doi: 10.1021/acs.joc.5b01637
21. [21]
  Cao, H.; Liu, X.-H.; Zhao, L.-M.; Cen, J.-H.; Lin, J.-X.; Zhu, Q.-X.; Fu, M.-L. Org. Lett. 2014, 16, 146. doi: 10.1021/ol4031414
22. [22]
  Liu, C.-R.; Ding, L.-H. Org. Biomol. Chem. 2015, 13, 2251. doi: 10.1039/C4OB02575J
23. [23]
  Azeredo, J. B.; Godoi, M.; Martins, G. M.; Silveira, C. C.; Braga, A. L. J. Org. Chem. 2014, 79, 4125. doi: 10.1021/jo5000779
24. [24]
  Ge, W.-L.; Wei, Y.-Y. Green Chem. 2012, 14, 2066. doi: 10.1039/c2gc35337g
25. [25]
  Sang, P.; Chen, Z.-K.; Zou, J.-W.; Zhang, Y.-H. Green Chem. 2013, 15, 2096. doi: 10.1039/c3gc40724a
26. [26]
  Yang, Y.; Zhang, S.; Tang, L.; Hu, Y.-B.; Zha, Z.-G.; Wang, Z.-Y. Green Chem. 2016, 18, 2609. doi: 10.1039/C6GC00313C
27. [27]
  Shen, C.; Zhang, P.-F.; Sun, Q.; Bai, S.-Q.; Andy Hor, T. S.; Liu, X.-G. Chem. Soc. Rev. 2015, 44, 291. doi: 10.1039/C4CS00239C
28. [28]
  Ma, Y.-Y.; Yan, Z.-Y.; Bian, C.-L.; Li, K.; Zhang, X.-W.; Wang, M.-F.; Gao, X.-L.; Zhang, H.; Lei, A.-W. Chem. Commun. 2015, 51, 10524. doi: 10.1039/C5CC02253C
29. [29]
  Nilsson, M.; Ullenius, C. Acta Chem. Scand 1966, 20, 423. doi: 10.3891/acta.chem.scand.20-0423
30. [30]
  Nilsson, M.; Ullenius, C. Acta Chem. Scand 1968, 22, 1998. doi: 10.3891/acta.chem.scand.22-1998
31. [31]
  Myers, A. G.; Tanaka, D.; Mannion, M. R. J. Am. Chem. Soc. 2002, 124, 11250. doi: 10.1021/ja027523m
32. [32]
  Tanaka, D.; Myers, A. G. Org. Lett. 2004, 6, 433. doi: 10.1021/ol0363467
33. [33]
  Gooßen, L. J.; Deng, G.-J.; Levy, L. M. Science 2006, 313, 662. doi: 10.1126/science.1128684
34. [34]
  Duan, Z.-Y.; Ranjit, S.; Zhang, P.-F.; Liu, X.-G. Chem. Eur. J. 2009, 15, 3666. doi: 10.1002/chem.200900133
35. [35]
  Sadananda, R.; Duan, Z.-Y.; Zhang, P.-F.; Liu, X.-G. Org. Lett. 2010, 12, 4134. doi: 10.1021/ol101729k
36. [36]
  Becht, J. M.; Drian, C. L. J. Org. Chem. 2011, 76, 6327. doi: 10.1021/jo200344w
37. [37]
  Xia, C.-C.; Wei, Z.-J.; Yang, Y.; Yu, W.-B.; Liao, H.-X.; Shen, C.; Zhang, P.-F. Chem. Asian J. 2016, 11, 360. doi: 10.1002/asia.v11.3
38. [38]
  Wang, P.-F.; Wang, X.-Q.; Dai, J.-J.; Feng, Y.-S.; Xu, H.-J. Org. Lett. 2014, 16, 4586. doi: 10.1021/ol502144c
39. [39]
  Xu, H.-J.; Lan, Q.-S.; Lin, Y.-C.; Li, Y.-Y.; Feng, Y.-S. Chin. J. Org. Chem. 2010, 30, 9(in Chinese).
40. [40]
  Suzuki, H.; Abe, H. Tetrahedron Lett. 1995, 36, 6239. doi: 10.1016/0040-4039(95)01095-Y
41. [41]
  Baskin, J. M.; Wang, Z.-Y. Org. Lett. 2002, 4, 4423. doi: 10.1021/ol0269190
42. [42]
  Bates, C. G.; Gujadhur, R. K.; Venkataraman, D. Org. Lett. 2002, 4, 2803. doi: 10.1021/ol0264105
43. [43]
  Carril, M.; SanMartin, R.; Domínguez, E.; Tellitu, I. Chem. Eur. J. 2007, 13, 5100. doi: 10.1002/(ISSN)1521-3765
44. [44]
  Feng, Y.-S.; Zhao, X.-Y.; Wang, J.-Y.; Zheng, F.-Y.; Xu, H.-J. Chin. J. Chem. 2009, 27, 2423(in Chinese).
45. [45]
  Yang, Y.; Li, W.-M.; Xia, C.-C.; Ying, B.-B.; Shen, C.; Zhang, P.-F. ChemCatChem. 2016, 8, 304 doi: 10.1002/cctc.201500917
46. [46]
  Ranjit, S.; Lee, R.; Heryadi, D.; Shen, C.; Wu, J.-E.; Zhang, P.-F.; Huang, K.-W.; Liu, X.-G. J. Org. Chem. 2011, 76, 8999. doi: 10.1021/jo2017444
47. [47]
  Zhang, H.; Cai, Q.; Ma, D.-W. J. Org. Chem. 2005, 70, 5164. doi: 10.1021/jo0504464
48. [48]
  Ouali, A.; Laurent, R.; Caminade, A. M.; Majoral, J. P.; Taillefer, M. J. Am. Chem. Soc. 2006, 128, 15990. doi: 10.1021/ja066505s
49. [49]
  Kwong, F. Y.; Buchwald, S. L. Org. Lett. 2002, 4, 3517. doi: 10.1021/ol0266673
50. [50]
  Kwong, F. Y.; Klapars, A.; Buchwald, S. L. Org. Lett. 2002, 4, 581. doi: 10.1021/ol0171867
51. [51]
  Gueiffier, C. E.; Thery, I.; Gueiffier, A.; Buchwald, S. L. Tetrahedron 2006, 62, 6042. doi: 10.1016/j.tet.2006.04.007
52. [52]
  Lv, X.; Bao, W.-L. J. Org. Chem. 2007, 72, 3863. doi: 10.1021/jo070443m
53. [53]
  Shafir, A.; Buchwald, S. L. J. Am. Chem. Soc. 2006, 128, 8742. doi: 10.1021/ja063063b
54. [54]
  Bates, C. G.; Saejueng, P.; Doherty, M. Q.; Venkataraman, D. Org. Lett. 2004, 6, 5005. doi: 10.1021/ol0477935
55. [55]
  Kabir, M. S.; Van Linn, M. L.; Monte, A.; Cook, J. M. Org. Lett. 2008, 10, 3363. doi: 10.1021/ol801149n
56. [56]
  Ma, D.-W.; Zhang, Y.-D.; Yao, J.-C.; Wu, S.-H.; Tao, F.-G. J. Am. Chem. Soc. 1998, 120, 12459. doi: 10.1021/ja981662f
57. [57]
  Ma, D.-W.; Xia, C.-F.; Jiang, J.-Q.; Zhang, J.-H. Org. Lett. 2001, 3, 2189. doi: 10.1021/ol016043h
58. [58]
  Ma, D.-W.; Xia, C.-F. Org. Lett. 2001, 3, 2583. doi: 10.1021/ol016258r
59. [59]
  Zhu, W.; Ma, D.-W. J. Org. Chem. 2005, 70, 2696. doi: 10.1021/jo047758b
60. [60]
  Deng, W.; Zou, Y.; Wang, Y.-F.; Liu, L.; Guo, Q.-X. Synlett. 2004, 7, 1254.
61. [61]
  Zhao, Q.; Shen, C.; Zheng, H.; Zhang, J.-C.; Zhang, P.-F. Carbohyd Res. 2010, 345, 437. doi: 10.1016/j.carres.2009.11.032
62. [62]
  Davis, A. P. Nature 2010, 464, 169. doi: 10.1038/464169a
63. [63]
  Shen, C.; Xia, H.-J.; Zheng, H.; Zhang, P.-F.; Chen, X.-Z. ChemInform 2011, 42, 1936.
64. [64]
  Shen, C.; Shen, F.-Y.; Xia, H.-J.; Zhang, P. F.; Chen, X.-Z. Tetrahedron:Asymmetry 2011, 22, 708. doi: 10.1016/j.tetasy.2011.04.007
65. [65]
  Shen, C.; Shen, F.-Y.; Zhou, G.-B.; Xia, H.-J.; Chen, X.-Z.; Liu, X.-G.; Zhang, P.-F. Catal. Commun. 2012, 26, 6. doi: 10.1016/j.catcom.2012.05.004
66. [66]
  Monopoli, A.; Calò, V.; Ciminale, F.; Cotugno, P.; Angelici, C.; Cioffi, N.; Nacci, A. J. Org. Chem. 2010, 75, 3908. doi: 10.1021/jo1005729
67. [67]
  Thakur, K. G.; Srinivas, K. S.; Chiranjeevi, K.; Sekar, G. ChemInform 2012, 43, 2326.
68. [68]
  Thakur, K. G.; Ganapathy, D.; Sekar, G. Chem. Commun. 2011, 42, 5076.
69. [69]
  Yang, M.; Shen, H.-Y.; Li, Y.-Y.; Shen, C.; Zhang, P.-F. RSC Adv. 2014, 4, 26295. doi: 10.1039/C4RA03187C
70. [70]
  Qiao, Z.-J.; Liu, H.; Xiao, X.; Fu, Y.; Wei, J.-P.; Li, Y.-X.; Jiang, X.-F. Org. Lett. 2013, 15, 2594 doi: 10.1021/ol400618k
71. [71]
  Cheng, Y.-N.; Peng, Q.; Fan, W.-G.; Li, P.-X. J. Org. Chem. 2014, 79, 5812. doi: 10.1021/jo5002752
72. [72]
  Yamamoto, T.; Sekine, Y. Can. J. Chem. 1984, 62, 1544. doi: 10.1139/v84-263
73. [73]
  Wang, X.-L.; Yang, F.; Xue, Z.-Y. Chin. J. Chem. 2015, 35, 29(in Chinese).
74. [74]
  Sperotto, E.; van Klink, G. P. M.; de Vries, J. G.; van Koten, G. J. Org. Chem. 2008, 73, 5625. doi: 10.1021/jo800491k
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