Articles

A Route to Alkynyl Sulfides and Asymmetric Disulfides from Sodium Arylsulfiniate

  • Lin Yamei ,
  • Yi Wenbin
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  • Chemical Engineering College, Nanjing University of Science & Technology, Nanjing 210094

Received date: 2017-11-21

  Revised date: 2017-12-17

  Online published: 2018-01-10

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21776138, 21476116), the Fundamental Research Funds for the Central Universities (No. 30916011102) and the Qing Lan and Six Talent Peaks in Jiangsu Province.

Abstract

A new approach for the synthesis of alkynyl sulfides and asymmetric disulfides with odorless, easy-to-handle sodium arylsulfiniates as the sulfur source in I2/PPh3 aqueous system has been developed. Compared with reported approaches, this protocol provides several merits including simple procedures, free of transition-metal catalysts and organic solvent, and high yields.

Cite this article

Lin Yamei , Yi Wenbin . A Route to Alkynyl Sulfides and Asymmetric Disulfides from Sodium Arylsulfiniate[J]. Chinese Journal of Organic Chemistry, 2018 , 38(5) : 1207 -1213 . DOI: 10.6023/cjoc201711036

References

[1] (a) Guillerm, G.; Guillerm, D.; Vandenplas-Witkowki, C.; Rogniaux, H.; Carte, N.; Leize, E.; Van Dorsselaer, A.; De Clercq, E.; Lambert, C. J. Med. Chem. 2001, 44, 2743.
(b) Cruz-Monteagudo, M.; PhamThe, H.; Cordeiro, M. N.; Borges, F. Mol. Inf. 2010, 29, 303.
(c) Kumar, R.; Srivastava, R.; Singh, R. K.; Surolia, A.; Rao, D. N. Bioorg. Med. Chem. 2008, 16, 2276.
[2] (a) Feng, M.; Jiang, X. Chem. Commun. 2014, 50, 9690.
(b) Nicolaou, K. C.; Hughes, R.; Pfefferkorn, J. A.; Barluenga, S.; Roecker, A. J. Chem.-Eur. J. 2001, 7, 4280.
(c) Conway, T. T.; DeMaster, E. G.; Goon, D. J. W.; Shirota, F. N.; Nagasawa, H. T. J. Med. Chem. 1999, 42, 4016.
(d) Nicolaou, K. C.; Lu, M.; Totokotsopoulos, S.; Heretsch, P.; Giguère, D.; Sun, Y.-P.; Sarlah, D.; Nguyen, T. H.; Wolf, I. C.; Smee, D. F.; Day, C. W.; Bopp, S.; Winzeler, E. A. J. Am. Chem. Soc. 2012, 134, 17320.
(e) Chankhamjon, P.; Boettger-Schmidt, D.; Scherlach, K.; Urbansky, B.; Lackner, G.; Kalb, D.; Dahse, H.-M.; Hoffmeister, D.; Hertweck, C. Angew. Chem., Int. Ed. 2014, 53, 13409.
(f) Mohammadi, M. K.; Ghammamy, S.; Zarrinabadi, S.; Farjam, M. H.; Sabayan, B. Chin. J. Chem. 2010, 28, 2199.
[3] (a) Bouillon, J.-P.; Musyanovich, R.; Portella, C.; Shermolovich, Y. Eur. J. Org. Chem. 2001, 3625.
(b) Hilt, G.; Luers, S.; Harms, K. J. Org. Chem. 2004, 69, 624.
(c) Ding, S.; Jia, G.; Sun, J. Angew. Chem., Int. Ed. 2014, 53, 1877.
(d) Savarin, C.; Srogl, J.; Liebeskind, L. S. Org. Lett. 2001, 3, 91.
(e) Wang, G.; Guo, Y.; Lü, Y.; Wang, X. C.; Quan, Z. J. Chin. J. Org. Chem. 2016, 36, 1375(in Chinese). (王刚, 郭燕, 吕颖, 王喜存, 权正军, 有机化学, 2016, 36, 1375.)
(f) 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.)
(g) Saba, S.; Rafique, J.; Braga, A. L. Catal. Sci. Technol. 2016, 6, 3087.
(h) Vieira, A. A.; Azeredo, J. B.; Godoi, M.; Santi, C.; da Silva Júnior, E. N.; Braga, A. L. J. Org. Chem. 2015, 80, 2120.
[4] (a) Yang, J.; Cohen Stuart, M. A.; Kamperman, M. Chem. Soc. Rev. 2014, 43, 8271.
(b) Wommack, A. J.; Ziarek, J. J.; Tomaras, J.; Chileveru, H. R.; Zhang, Y.; Wagner, G.; Nolan, E. M. J. Am. Chem. Soc. 2014, 136, 13494.
(c) Ge, W. W.; Chen, J.; Zhang, Y.; Zong, L.; Zhang, M.; Dong, J. J. Chin. J. Org. Chem. 2017, 37, 2409(in Chinese). (葛巍巍, 陈静, 张也, 宗良, 张鸣, 董俊军, 有机化学, 2017, 37, 2409.)
[5] (a) Rowan, S. J.; Cantrill, S. J.; Cousins, G. R. L.; Sanders, J. K. M.; Stoddart, J. F. Angew. Chem., Int. Ed. 2002, 41, 898.
(b) Otto, S.; Furlan, R. L. E.; Sanders, J. K. M. Science 2002, 297, 590.
[6] (a) Doroszuk, J.; Musiejuk, M.; Demkowicz, S.; Rachon, J.; Witt, D. RSC Adv. 2016, 6, 105449.
(b) Takeda, H.; Shimada, S.; Ohnishi, S.; Nakanishi, F.; Matsuda, H. Tetrahedron Lett. 1998, 39, 3701.
[7] (a) Fang, Z.; He, W.; Cai, M.; Lin, Y.; Zhao, H. Tetrahedron Lett. 2015, 56, 6463.
(b) Arisawa, M.; Fujimoto, K.; Morinaka, S.; Yamaguchi, M. J. Am. Chem. Soc. 2005, 127, 12226.
(c) Braga, A. L.; Silviera, C. C.; Reckziegel, A.; Menezes, P. H. Tetrahedron Lett. 1993, 34, 8041.
(d) Bieber, L. W.; da Silva, M. F.; Menezes, P. H. Tetrahedron Lett. 2004, 45, 2735.
[8] Frei, R.; Wodrich, M. D.; Hari, D. P.; Borin, P.-A.; Chauvier, C.; Waser, J. J. Am. Chem. Soc. 2014, 136, 16563.
[9] (a) Ziegler, G. R.; Welch, C. A.; Orzech, C. E.; Kikkawa, S.; Miller, S. I. J. Am. Chem. Soc. 1963, 85, 1648.
(b) Marchueta, I.; Montenegro, E.; Panov, D.; Poch, M.; Verdaguer, X.; Moyano, A.; Pericas, M. A.; Riera, A. J. Org. Chem. 2001, 66, 6400.
(c) Ni, Z.; Wang, S.; Mao, H.; Pan, Y. Tetrahedron Lett. 2012, 53, 3907.
(d) Ochiai, M.; Nagaoka, T.; Sueda, T.; Yan, J.; Chen, D. W.; Miyamoto, K. Org. Biomol. Chem. 2003, 1, 1517.
[10] (a) Taniguchi, N. Tetrahedron 2017, 73, 2030.
(b) Field, L.; Buckman, J. D. J. Org. Chem. 1968, 33, 3865.
(c) Brzezinska, E.; Ternay, A. L. J. Org. Chem. 1994, 59, 8239.
(d) Zhao, R. Y.; Erickson, H. K.; Leece, B. A.; Reid, E. E.; Goldmacher, V. S.; Lambert, J. M.; Chari, R. V. J. J. Med. Chem. 2012, 55, 766.
(e) Sivaramakrishnan, S.; Keerthi, K.; Gates, K. S. J. Am. Chem. Soc. 2005, 127, 10830.
[11] Vandavasi, J. K.; Hu, W.-P.; Chen, C.-Y.; Wang, J.-J. Tetrahedron 2011, 67, 8895.
[12] Arisawa, M.; Yamaguchi, M. J. Am. Chem. Soc. 2003, 125, 6624.
[13] Xiao, X.; Feng, M.; Jiang, X. Chem. Commun. 2015, 51, 4208.
[14] (a) Xiao, X.; Feng, M.; Jiang, X. Angew. Chem., Int. Ed. 2016, 55, 14121.
(b) Dai, Z.; Xiao, X.; Jiang, X. Tetrahedron 2017, 73, 3702.
[15] (a) Lin, Y.-M.; Lu, G.-P.; Cai, C.; Yi, W.-B. Org. Lett. 2015, 17, 3310.
(b) Lin, Y.-M.; Lu, G.-P.; Wang, G.-X.; Yi, W.-B. Adv. Synth. Catal. 2016, 358, 4100.
(c) Lin, Y.-M.; Lu, G.-P.; Wang, G.-X.; Yi, W.-B. J. Org. Chem. 2017, 82, 382.
(d) Xu, Z.-B.; Lu, G.-P.; Cai, C. Org. Biomol. Chem. 2017, 15, 2804.
[16] Ni, Z.; Wang, S.; Mao, H.; Pan, Y. Tetrahedron Lett. 2012, 53, 3907.
[17] Yang, Y.; Dong, W.; Guo, Y.; Rioux, R. M. Green Chem. 2013, 15, 3170.
[18] Liu, F.; Yi, W. Org. Chem. Front. 2018, 5, 428.
[19] Peña, J.; Talavera, G.; Waldecker, B.; Alcarazo, M. Chem.-Eur. J. 2017, 23, 75.
[20] Han, M.; Lee, J. T.; Hahn, H.-G. Tetrahedron Lett. 2011, 52, 236.
[21] Bao, M.; Shimizu, M. Tetrahedron 2003, 59, 9655.
[22] Demkowicz, S.; Rachon, J.; Witt, D. Synthesis 2008, 350, 2033.
[23] Turos, E.; Revell, K. D.; Ramaraju, P.; Gergeres, D. A.; Greenhalgh, K.; Young, A.; Sathyanarayan, N.; Dickey, S.; Lim, D.; Alhamadsheh, M. M.; Reynolds, K. Bioorg. Med. Chem. 2008, 16, 6501.
[24] Hunter, R.; Caira, M.; Stellenboom, N. J. Org. Chem. 2006, 71, 8268.
[25] Tsutsumi, N.; Itoh, T.; Ohsawa, A. Chem. Pharm. Bull. 2000, 48, 1524.
[26] Benati, L.; Montevecchi, P. C.; Spagnolo, P. Tetrahedron Lett. 1986, 27, 1739.

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