Citation: Huang Cheng-Mi, Li Jian, Wang Shun-Yi, Ji Shun-Jun. TFA promoted multi-component reaction of aryldiazonium with sodium metabisulphite and thiols: Construction of thiosulfonate under transition-metal free conditions[J]. Chinese Chemical Letters, ;2020, 31(7): 1923-1926. doi: 10.1016/j.cclet.2019.12.032 shu

TFA promoted multi-component reaction of aryldiazonium with sodium metabisulphite and thiols: Construction of thiosulfonate under transition-metal free conditions

Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science & Collaborative Innovation Center of Suzhou Nano Science and Technology, Soochow University, Suzhou 215123, China

shunyi@suda.edu.cn

shunjun@suda.edu.cn

chemjsj@suda.edu.cn

Received Date: 17 October 2019
Revised Date: 11 December 2019
Accepted Date: 24 December 2019
Available Online: 24 December 2019

Figures(6)

A TFA promoted multi-component reaction of aryldiazonium with sodium metabisulphite and thiols to construct thiosulfonates under transition-metal free conditions is reported. The thiosulfonates were isolated in good yields with broad tolerance of functional group. Readily available inorganic Na₂S₂O₅ was applied as the sulfur dioxide surrogate. This strategy features easily available substrates, mild reaction conditions and free transition-metal catalyst.
- Metal-free,
- Thiosulfonate,
- Sulfur dioxide,
- Sodium metabisulfite
1. [1]
  (a) J.P. Weidner, S.S. Block, J. Med. Chem. 7(1964) 671-673;
  (b) S.S. Block, J.P. Weidner, Dev. Ind. Microbiol. 4(1963) 213-217;
  (c) N.S. Zefirov, N.V. Zyk, E.K. Beloglazkina, A.G. Kutateladze, Sulfur Rep. 14(1993) 223-240;
  (d) P. Natarajan, Tetrahedron Lett. 56(2015) 4131-4134.
2. [2]
  (a) B.M. Trost, Chem. Rev. 78(1978) 363-382;
  (b) M.G. Ranasinghe, P.L. Fuchs, Synth. Commun. 18(1988) 227-230;
  (c) K. Fujiki, E. Yoshida, Synth. Commun. 29(1999) 3289-3294;
  (d) K. Fujiki, S. Akieda, H. Yasuda, Y. Sasaki, Synthesis 7(2001) 1035-1042;
  (e) S. Kim, S. Kim, N. Otsuka, I. Ryu, Angew. Chem. Int. Ed. 44(2005) 6183-6186;
  (f) V. Girijavallabhan, C. Alvarezand, F.G. Njoroge, J. Org. Chem. 76(2011) 6442-6446;
  (g) Z.H. Peng, X. Zheng, Y.J. Zhang, D.L. An, W.R. Dong, Green Chem. 20(2018) 1760-1764.
3. [3]
  (a) L. Field, T.F. Parsons, J. Org. Chem. 30(1965) 657-659;
  (b) E. Block, J.O.' Connor, J. Am. Chem. Soc. 96(1974) 3921-3929;
  (c) Y. Wang, J.H. Espenson, J. Org. Chem. 65(2000) 104-107;
  (d) V. Nair, A. Augustine, Org. Lett. 5(2003) 543-544;
  (e) M.T. Cai, G.S. Lv, J.X. Chen, et al., Chem. Lett. 39(2010) 368-369;
  (f) S. Sobhani, S. Aryanejad, M.F. Maleki, Synlett (2011) 319-322;
  (g) M. Kirihara, S. Naito, Y. Ishizuka, H. Hanai, T. Noguchi, Tetrahedron Lett. 52(2011) 3086-3089;
  (h) K. Bahrami, M.M. Khodaei, D. Khaledian, Tetrahedron Lett. 53(2012) 354-358;
  (i) M. Kirihara, S. Naito, Y. Nishimura, Y. Ishizuka, et al., Tetrahedron 70(2014) 2464-2471;
  (j) T.X.T. Luu, T.T.T. Nguyen, T.N. Le, J. Spanget-Larsen, F. Duus, J. Sulfur. Chem. 36(2015) 340-350;
  (k) P.K. Shyam, Y.K. Kim, C. Lee, H.Y. Jang, Adv. Synth. Catal. 358(2016) 56-61.
4. [4]
  (a) Y.L. Yang, B. Rajagopal, C.F. Liang, et al., Tetrahedron 69(2013) 2640-2646;
  (b) Y. Liu, Y. Zhang, Tetrahedron Lett. 44(2003) 4291-4294;
  (c) G. Kumaraswamy, R. Raju, V. Narayanarao, RSC Adv. 5(2015) 22718-22723.
5. [5]
  M. Xia, Z.C. Chen, Synth. Commun. 27(1997) 1309.
6. [6]
  (a) M.D. Bentley, I.B. Douglass, J.A. Lacadie, J. Org. Chem. 37(1972) 333-334;
  (b) T. Billard, B.R. Langlois, S. Large, et al., J. Org. Chem. 61(1996) 7545-7550;
  (c) K. Fujiki, N. Tanifuji, Y. Sasaki, T. Yokoyama, Synthesis 3(2002) 343-348;
  (d) G. Liang, M. Liu, et al., Chin. J. Chem. 30(2012) 1611-1616;
  (e) G. Liang, J. Chen, J. Chen, et al., Tetrahedron Lett. 53(2012) 6768-6770.
7. [7]
  (a) N. Taniguchi, J. Org. Chem. 80(2015) 1764-1770;
  (b) G.Y. Zhang, S.S. Lv, A. Shoberu, J.P. Zou, J. Org. Chem. 82(2017) 9801-9807;
  (c) Z.H. Peng, X. Zheng, Y.J. Zhang, D.L. An, W.R. Dong, Green Chem. 20(2018) 1760-1764;
  (d) Q. Chen, Y.L. Huang, X.F. Wang, J.W. Wu, G.D. Yu, Org. Biomol. Chem. 16(2018) 1713-1719.
8. [8]
  L. Cao, S.H. Luo, K. Jiang, et al., Org. Lett. 20(2018) 4754-4758.
9. [9]
  (a) Z.Y. Mo, T.R. Swaroop, Z.F. Chen, et al., Green Chem. 20(2018) 4428-4432;
  (b) X.F. Zhang, C. Cui, Y.H. Zhang, et al., Adv. Synth. Catal. 361(2019) 2014-2019.
10. [10]
  (a) M. Luo, X.H. Zhang, D. Darensbourg, Acc. Chem. Res. 49(2016) 2209-2219;
  (b) G. Adaros, H.J. Weigel, H.J. Jauger, New Phytol. 108(1988) 67-74.
11. [11]
  B. Nguyen, E.J. Emmett, M.C. Willis, J. Am. Chem. Soc. 132(2010) 16372-16373.
12. [12]
  (a) F.S. He, Y.Q. Wu, X.F. Li, H.G. Xia, J. Wu, Org. Chem. Front. 6(2019) 1873-1878;
  (b) X.F. Wang, M. Yang, W.L. Xie, X.N. Fan, Jie Wu, Chem. Commun. 55(2019) 6010-6013;
  (c) J. Zhang, W.L. Xie, S.Q. Ye, J. Wu, Org. Chem. Front. 6(2019) 1863-1867;
  (d) Y. Zong, Y.M. Lang, M. Yang, et al., Org. Lett. 21(2019) 1935-1938;
  (e) S.Q. Ye, D.Q. Zheng, J. Wu, G.Y.S. Qiu, Chem. Commun. 55(2019) 2214-2217;
  (f) X.F. Wang, H.Z. Li, G.Y.S. Qiu, J. Wu, Chem. Commun. 55(2019) 2062-2065;
  (g) D.Q. Zheng, J. Yu, J. Wu, Angew. Chem. Int. Ed. 55(2016) 11925-11929;
  (h) F. Liu, J.Y. Wang, B. Jiang, et al., Angew. Chem. Int. Ed. 56(2017) 15570-15574;
  (i) K.D. Zhou, J. Zhang, G.Y.S. Qiu, J. Wu, Org. Lett. 21(2019) 275-278;
  (j) H.J. Chen, M.L. Liu, G.Y.S. Qiu, J. Wu, Adv. Synth. Catal. 361(2019) 146-150;
  (k) S. Ye, J. Wu, Chem. Commun. 48(2012) 7753-7755;
  (l) X.Y. Qin, L. He, J. Li, B. Jiang, et al., Chem. Commun. 55(2019) 3227-3230;
  (m) S. Liu, K. Chen, W.J. Hao, et al., J. Org. Chem. 84(2019) 1964-1971;
  (n) Z.J. Shen, Y.N. Wu, C.L. He, et al., Chem. Commun. 54(2018) 445-448;
  (o) T.H. Zhu, X.C. Zhang, K. Zhao, T.P. Loh, Org. Chem. Front. 6(2019) 94-98;
  (p) T.H. Zhu, X.C. Zhang, X.L. Cui, et al., Adv. Synth. Catal. 361(2019) 1-7.
13. [13]
  (a) G. Li, Z. Gan, K. Kong, X. Dou, D. Yang, Adv. Synth. Catal. 361(2019) 1808-1814;
  (b) A.M. Nair, S. Kumar, L. Halder, C.M.R. Volla, Org. Biomol. Chem. 17(2019) 5897-5901.
14. [14]
  (a) X.X. Gong, J.H. Chen, L.F. Lai, et al., Chem. Commun. 54(2018) 11172-11175;
  (b) H.T. Dang, V.T. Nguyen, V.D. Nguyen, H.D. Armana, O.V. Larionov, Org. Biomol. Chem. 16(2018) 3605-3609;
  (c) M. Wang, J.Y. Zhao, X.F. Jiang, ChemSusChem 12(2019) 3064-3068;
  (d) X.X. Gong, M.J. Wang, S.Q. Ye, J. Wu, Org. Lett. 21(2019) 1156-1160;
  (e) G.Y.S. Qiu, K.D. Zhou, J. Wu, Chem. Commun. 54(2018) 12561-12569;
  (f) M. Wang, Q.L. Fan, X.F. Jiang, Green Chem. 20(2018) 5469-5473.
15. [15]
  (a) U.M.V. Basavanag, A. Dos Santos, L. El Kaim, R. Gamez Montano, L. Grimaud, Angew. Chem. Int. Ed. 52(2013) 7194-7197;
  (b) D. Koziakov, A.J.V. Wangelin, Org. Biomol. Chem. 15(2017) 6715-6719;
  (c) F.P. Crisostomo, T. Martin, R. Carrillo, Angew. Chem. Int. Ed. 53(2014) 2181-2185;
  (d) M. Hartmann, Y. Li, A. Studer, J. Am. Chem. Soc. 134(2012) 16516-16519;
  (e) R. Huisgen, L. Krause, Ann. Chem. 574(1951) 157-171;
  (f) D. Koziakov, G.J. Wu, A.J. von Wangelin, Org. Biomol. Chem. 16(2018) 4942-4953;
  (g) N. Naveen, S. Sengupta, S. Chandrasekaran, J. Org. Chem. 83(2018) 3562-3569;
  (h) S.L. Yi, M.C. Li, X.Q. Hu, W.M. Mo, Z.L. Shen, Chin. Chem. Lett. 27(2016) 1505-1508;
  (i) H.X. Xu, Q.C. Wang, Chin. Chem. Lett. 30(2019) 337-339;
  (j) K.B. Ouyang, W. Hao, W.X. Zhang, Z.F. Xi, Chem. Rev. 115(2015) 12045-12090;
  (k) Q.J. Wang, Y.J. Su, L.X. Li, H.M. Huang, Chem. Soc. Rev. 45(2016) 1257-1272;
  (l) D. Koziakov, A.J. von Wangelin, Org. Biomol. Chem. 15(2017) 6715-6719.
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