Citation: Guo Fangjie, He Yuxuan, Wang Jingyun, Sun Jing, Zhou Mingdong. Potassium tert-Butoxide Promoted Formation of Alkyl Aryl Thioethers at Room Temperature: Synthesis and Mechanism[J]. Chinese Journal of Organic Chemistry, ;2017, 37(6): 1556-1559. doi: 10.6023/cjoc201612003 shu

Potassium tert-Butoxide Promoted Formation of Alkyl Aryl Thioethers at Room Temperature: Synthesis and Mechanism

School of Chemistry and Materials Science, Liaoning Shihua University, Fushun 113001

Corresponding author: Sun Jing, sunjing@lnpu.edu.cn Zhou Mingdong, mingdong.zhou@lnpu.edu.cn
Received Date: 2 December 2016
Revised Date: 14 January 2017

Fund Project: the Fushun Science & Technology Program FSKJHT201423the National Natural Science Foundation of China 21101085the Natural Science Foundation of Liaoning Province 2015020196the Liaoning Excellent Talents Program in University LJQ2012031the Talent Scientific Research Fund of Liaoning Shihua University 2016XJJ-006

The C—S cross-coupling of aryl halides with alkyl thiols under transition metal-free conditions was investigated. Good to excellent yields can be obtained for a variety of electron-poor aryl halides with alkyl thiols in the presence of KO^tBu even at room temperature. The mechanisms for transition metal-free coupling reactions are discussed.
- C—S cross-coupling,
- aryl halides,
- mechanism,
- alkyl aryl thioethers
1. [1]
  (a) Yao, H. ; Richardson, D. E. J. Am. Chem. Soc. 2003, 125, 6211.
  (b) Qin, Z. ; Kastrati, I. ; Chandrasena, R. E. P. ; Liu, H. ; Yao, P. ; Petukhov, P. A. ; Bolton, J. L. ; Thatcher, G. R. J. J. Med. Chem. 2007 50, 2682.
  (c) Bagley, M. C. ; Davis, T. ; Dix, M. C. ; Rokicki, M. ; Kipling, D. Bioorg. Med. Chem. Lett. 2007, 17, 5107.
  (d) Bryan, C. S. ; Braunger, J. A. ; Lautens, M. Angew. Chem. Int. Ed. 2009, 121, 7198.
  (e) Beletskaya, I. P. ; Ananikov, V. P. Chem. Rev. 2011, 111, 1596.
  (f) Ubale, A. U. ; Bhute, M. V. ; Malpe, G. P. ; Raut, P. P. ; Chipade, K. S. ; Ibrahim, S. G. J. Sadui Chem. Soc. 2016, 20, 227.
  (g) Zhou, Y. B. ; Gao, F. ; Zhao, Y. ; Lu, J. J. Sadui Chem. Soc. 2014, 18, 589.
  (h) Zaafarany, I. ; Boller, H. J. Sadui Chem. Soc. 2010, 14, 183.
  (i) An, Y. N. ; Li, J. X. ; Li, M. . ; Li, C. S. ; Yang, S. R. Chin. J. Org. Chem. 2017, 37, 720(in Chinese).
  (安艳妮, 李建晓, 李蒙, 李春生, 杨少容, 有机化学, 2017, 37, 720. )
2. [2]
  (a) Byeun, A.; Baek, K.; Han, M. S.; Lee, S. Tetrahedron Lett. 2013, 54, 6712.
  (b) Alvaroa, E.; Hartwig, J. F. J. Am. Chem. Soc. 2009, 131, 7858.
  (c) Li, J. X.; Li, C. S.; Yang, S. R.; An, Y. N.; Wu, W. Q.; Jiang, H. F. J. Org. Chem. 2016, 81, 2875.
  (d) Li, J. X.; Li, C. S.; Yang, S. R.; An, Y. N.; Wu, W. Q.; Jiang, H. F. J. Org. Chem. 2016, 81, 7771.
3. [3]
  (a) Luo, F.; Pan, C.; Li, L. P.; Chen, F.; Cheng, J. Chem. Commun. 2011, 47, 5304.
  (b) Mallick, S.; Rana, S.; Parida, K. Dalton. Trans. 2011, 40, 9169.
4. [4]
  (a) Zhang, J.; Medley, C. M.; Krause, J. A.; Guan, H. Organometallics 2010, 29, 6393.
  (b) Venkanna, G. T.; Arman, H. D.; Tonzetich, Z. J. ACS Catal. 2014, 4, 2941.
  (c) Jammi, S.; Barua, P.; Rout, L.; Saha, P.; Punniyamurthy, T. Tetrahedron Lett. 2008, 49, 1484.
  (d) Baldovino-Pantaleón, O.; Hernández-Ortega, S.; Morales-Mo-rales, D. Adv. Syn. Catal. 2006, 348, 236. (e) Guan, P.; Cao, C.; Liu, Y.; Li, Y.; He, P.; Chen, Q.; Liu, G.; Shi, Y. Tetrahedron Lett. 2012, 53, 5987.
5. [5]
  (a) Zhang, Y. G.; Ngeow, K. C.; Ying, J. Y. Org. Lett. 2007, 9, 3495.
  (b) Yuan, Y.; Thomé, I.; Kim, S. H.; Chen, D.; Beyer, A.; Bonnamour, J.; Zuidema, E.; Chang, S.; Bolm, C. Adv. Synth. Catal. 2010, 352, 2892.
  (c) Cano, R.; Ramón, D. J.; Yus, M. J. Org. Chem. 2011, 76, 654.
  (d) Duan, Z.; Ranjit, S.; Liu, X. Org. Lett. 2010, 12, 2430.
6. [6]
  (a) Shi, Y.; Cai, Z.; Guan, P.; Pang, G. Synth. Let. 2011, 22, 2090.
  (b) Fu, C. F.; Liu, Y. H.; Peng, S. M.; Liu, S. T. Tetrahedron 2010, 66, 2119.
  (c) Ma, D.; Geng, Q.; Zhang, H.; Jiang, Y. Angew. Chem., Int. Ed. 2010, 49, 1291.
  (d) Xu, R.; Wan, J. P.; Mao, H.; Pan, Y. J. Am. Chem. Soc. 2010, 132, 15531.
  (e) Wu, J. R.; Lin, C. H.; Lee, C. F. Chem. Commun. 2009, 29, 4450.
  (f) Iglesias, M. J.; Prieto, A.; Nicasio, M. C. Adv. Synth. Catal. 2010, 352, 949.
7. [7]
  (a) Bradshaw, J. S.; Chen, E. Y.; Hales, R. H.; South, J. A. J. Org. Chem. 1972, 37, 2051.
  (b) March, J. Advanced Organic Chemistry, Vol. 4, John Wiley & Sons, Inc, New York, 1985, p. 576.
  (c) Varala, R.; Ramu, E.; Alam, M. M.; Adapa, S. R. Chem. Lett. 2004, 33, 1614.
8. [8]
  Sun, C.; Li, H.; Yu, D.; Yu, M.; Zhou, X.; Lu, X.; Huang, K.; Zheng, S.; Li, B.; Shi, Z. Nat. Chem. 2010, 2, 044.
9. [9]
  Liu, W.; Cao, H.; Zhang, H.; Zhang, H.; Chung, K. H.; He, C.; Wang, H.; Kong, F. Y.; Lei, A. J. Am. Chem. Soc. 2010, 132, 16737. doi: 10.1021/ja103050x
10. [10]
  Shirakawa, E.; Itoh, K.; Higashino, T.; Hayashi, T. J. Am. Chem. Soc. 2010, 132, 15537. doi: 10.1021/ja1080822
11. [11]
  (a) Wei, W. T.; Liu, Y.; Ye, L. M.; Lei, R. H.; Zhang, X. J.; Yan, M. Org. Biomol. Chem. 2015, 13, 817. (b) Chen, Y. Y.; Zhang, N. N.; Ye, L. M.; Chen, J. H.; Shun, X.; Zhang, X. J.; Yan, M. RSC Adv. 2015, 5, 48046.
12. [12]
  Qiao, Z.; Wei, J.; Jiang, X. Org. Lett. 2014, 16, 1212. doi: 10.1021/ol500112y
13. [13]
  Xu, J. A.; Wei, T. Z.; Xia, J. K.; Zhang, Q. H.; Wu, H. S. Chirality 2004, 16, 341. doi: 10.1002/(ISSN)1520-636X
14. [14]
  Zhang, H.; Cao, W. G.; Ma, D. W. Synth. Commun. 2007, 37, 25.
15. [15]
  Martyn, J.; Soren, L. B.; Mogens, B. N. J. Org. Chem. 2013, 78, 4348. doi: 10.1021/jo400362u
16. [16]
  Gorczynski, M. J.; Leal, R. M.; Mooberry, S. L.; Bushweller, J. H.; Brown, M. L. Bioorg. Med. Chem. 2004, 12, 1029. doi: 10.1016/j.bmc.2003.12.003
17. [17]
  Jean, M.; Renault, J.; Weghe, P. V. D.; Asao, N. Tetrahedron Lett. 2010, 51, 378. doi: 10.1016/j.tetlet.2009.11.025
18. [18]
  Taniguchi, N.; Onami, T. J. Org. Chem. 2004, 69, 915. doi: 10.1021/jo030300+
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