Chinese Journal of Organic Chemistry >
Metal-Free Thiomethylation of α-Oxoketene Dithioacetals
Received date: 2017-01-25
Revised date: 2017-03-17
Online published: 2017-04-10
Supported by
Project supported by the National Natural Science Foundation of China (Nos. 21172197, 21372201) and the Opening Foundation of Zhejiang Key Course of Chemical Engineering and Technology, Zhejiang University of Technology.
With dimethyl sulfoxide (DMSO) as a source of thiomethyl group and NH4I as a promotor, the thiomethylation of α-oxoketene dithioacetals has been achieved to afford thiomethylated α-oxoketene dithioacetals in moderate to good yields. The optimized reaction conditions were established through systematic investigations of solvents, temperature, time, promotors and their dosages in the reaction. The present reaction has advantages of easy availability of starting materials, simple operation, good compatibility of substrates, and metal-free reaction conditions.
Key words： DMSO; α-oxoketene dithioacetals; thiomethylation; metal-free
Zhang Haifeng , Bao Hanyang , Xu Zheng , Liu Yunkui . Metal-Free Thiomethylation of α-Oxoketene Dithioacetals[J]. Chinese Journal of Organic Chemistry, 2017 , 37(8) : 2153 -2158 . DOI: 10.6023/cjoc201701048
[1] (a) Dieter, R. K. Tetrahedron 1986, 42, 3029.
(b) Junjappa, H.; Ila, H.; Asokan, C. V. Tetrahedron 1990, 46, 5423.
(c) Kolb, M. Synthesis 1997, 357.
(d) Yakoyama, M.; Imamoto, T. Synthesis 1984, 797.
[2] (a) Charanraj, T. P.; Ramachandra, P.; Ramesh, N.; Junjappa, H. Tetrahedron Lett. 2016, 57, 3264.
(b) Deshmukh, G.; Kalyankar, S.; Kalyankar, M. J. Chem., Biol. Phys. Sci. 2015, 5, 1185.
[3] (a) Monnier, F.; Taillefer, M. Angew. Chem., Int. Ed. 2008, 47, 3096.
(b) Gademann, K.; Portmann, C.; Blom, J. F.; Zeder, M.; Jüttner, F. J. Nat. Prod. 2010, 73, 980.
(c) Halim, M.; Yee, D. J.; Sames, D. J. Am. Chem. Soc. 2008, 130, 14123.
(d) Pedras, M. S. C.; Zaharia, I. L. Org. Lett. 2001, 3, 1213.
(e) Pedras, M. S. C.; Zheng, Q. A.; Strelkov, S. J. Agric. Food Chem. 2008, 56, 9949.
(f) Wilson, A. J.; Kerns, J. K.; Callahan, J. F.; Moody, C. J. J. Med. Chem. 2013, 56, 7463.
[4] (a) Chen, X.; Hao, X. S.; Goodhue, C. E.; Yu, J. Q. J. Am. Chem. Soc. 2006, 128, 6790.
(b) Martinek, M.; Korf, M.; Srogl, J. Chem. Commun. 2010, 46, 4387.
(c) Saidi, O.; Marafie, J.; Ledger, A. E.; Liu, P. M.; Mahon, M. F.; Kociok-Köhn, G.; Whittlesey, M. K.; Frost, C. G. J. Am. Chem. Soc. 2011, 133, 19298.
(d) Umierski, N.; Manolikakes, G. Org. Lett. 2013, 15, 4972.
(e) Wu, Z.; Song, H.; Cui, X.; Pi, C.; Du, W.; Wu, Y. Org. Lett. 2013, 15, 1270.
(f) Zhao, X.; Dimitrijevic, E.; Dong, V. M. J. Am. Chem. Soc. 2009, 131, 3466.
[5] Chen, X.; Hao, X. S.; Goodhue, C. E.; Yu, J. Q. J. Am. Chem. Soc. 2006, 128, 6790.
[6] Chu, L.; Yue, X.; Qing, F. L. Org. Lett. 2010, 12, 1644.
[7] Taniguchi, N.; Onami, T. J. Org. Chem. 2004, 69, 915.
[8] Kumar, S.; Engman, L. J. Org. Chem. 2006, 71, 5400.
[9] Gao, X. F.; Pan, X. J.; Gao, J.; Jiang, H. F.; Yuan, G. Q.; Li, Y. W. Org. Lett. 2015, 17, 1038.
[10] Dai, C.; Xu, Z.; Huang, F.; Yu, Z.; Gao, Y. F. J. Org. Chem. 2012, 77, 4414.
[11] Li, X.; Xu, Y.; Wu, W.; Jiang, C.; Qi, C.; Jiang, H. Chem. Eur. J. 2014, 20, 7911.
[12] Luo, F.; Pan, C.; Li, L.; Chen, F.; Cheng, J. Chem. Commun. 2011, 47, 5304.
[13] Reeves, J. T.; Camara, K.; Han, Z. S.; Xu, Y.; Lee, H.; Busacca, C. A.; Senanayake, C. H. Org. Lett. 2014, 16, 1196.
[14] Timpa, S. D.; Pell, C. J.; Ozerov, O. V. J. Am. Chem. Soc. 2014, 136, 14772.
[15] Luo, F.; Pan, C.; Li, L.; Chen, F.; Cheng, J. Chem. Commun. 2011, 47, 5304.
[16] Chu, L.; Yue, X.; Qing, F. L. Org. Lett. 2010, 12, 1644.
[17] Liu, F. L.; Chen, J. R.; Zou, Y. Q.; Wei, Q.; Xiao, W. J. Org. Lett. 2014, 16, 3768.
[18] Patil, S. M.; Kulkarni, S.; Mascarenhas, M.; Sharma, R.; Roopan, S. M.; Roychowdhury, A. Tetrahedron 2013, 69, 8255.
[19] Keddie, D. J.; Johnson, T. E.; Arnold, D. P.; Bottle, S. E. Org. Biomol. Chem. 2005, 3, 2593.
[20] Kondo, T.; Kirschenbaum, L. J.; Kim, H.; Riesz, P. J. Phys. Chem. 1993, 97, 522.
[21] Ren, X.; Chen, J.; Chen, F.; Cheng, J. Chem. Commun. 2011, 47, 6725.
[22] Zhang, Z.; Tian, Q.; Qian, J.; Liu, Q.; Liu, T.; Shi, L.; Zhang, G. J. Org. Chem. 2014, 79, 8182.
[23] Zhu, L. P.; Yu, H. M.; Guo, Q. P.; Chen, Q.; Xu, Q.; Wang R. Org. Lett. 2015, 17, 1978.
[24] Meng, T.; Feng, C.; Liu, L.; Wang, T.; Xu, K.; Zhao, W. Chin. J. Org. Chem. 2016, 36, 1382(in Chinese). (孟团结, 冯翠兰, 刘澜涛, 王涛, 许凯, 赵文献, 有机化学, 2016, 36, 1382.)
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