Synthesis 2017; 49(07): 1575-1582
DOI: 10.1055/s-0036-1588918
paper
© Georg Thieme Verlag Stuttgart · New York

Copper(II)-Catalyzed Chemo- and Stereocontrolled Synthesis of (E)-Vinyl Sulfones and (Z)-β-Chlorovinyl Sulfones from Terminal Alkynes and Arylsulfonyl Hydrazides

Xiao-Tao Liu*
a  Huaian Wanbang Aromatic Chemicals Industry Co., Ltd. Huaian, Jiangsu, P. R. of China   Email: Xiaotao.Liu@wxintl.com
,
Zong-Cang Ding
b  Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, Fujian, P. R. of China   Email: zpzhan@xmu.edu.cn
,
Lu-Chuan Ju
b  Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, Fujian, P. R. of China   Email: zpzhan@xmu.edu.cn
,
Su-Xia Xu
b  Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, Fujian, P. R. of China   Email: zpzhan@xmu.edu.cn
,
Zhuang-Ping Zhan*
b  Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, Fujian, P. R. of China   Email: zpzhan@xmu.edu.cn
› Author Affiliations
Further Information

Publication History

Received: 02 September 2016

Accepted after revision: 01 November 2016

Publication Date:
06 December 2016 (online)


Abstract

A facile copper(II)-catalyzed regio- and stereocontrolled synthesis of vinyl sulfones from terminal alkynes and arylsulfonyl hydrazides is described. Depending on the source of copper(II), two different kinds of vinyl sulfones, (E)-vinyl sulfones and (Z)-β-chlorovinyl sulfones were obtained and the addition of cyclohexanone played an important role in the reaction. These reactions display excellent chemoselectivity as well as stereoselectivity.

Supporting Information

 
  • References

    • 1a Simpkins NS. Sulphones in Organic Synthesis . Pergamon; Oxford: 1993
    • 1b Tanaka K, Kaji A. The Chemistry of Sulfones and Sulphoxides . Patai S, Rapoport Z, Stirling CJ. M. Wiley; Chichester: 1988: 15
    • 1c Carreno MC. Chem. Rev. 1995; 95: 1717
    • 1d Yoshida K, Hayashi T. J. Am. Chem. Soc. 2003; 125: 2872
    • 1e Noshi MN, El-Awa A, Torres E, Fuchs PL. J. Am. Chem. Soc. 2007; 129: 11242
    • 1f Desrosiers JN, Charette AB. Angew. Chem. Int. Ed. 2007; 46: 5955
    • 1g Pandey G, Tiwari KN, Puranik VG. Org. Lett. 2008; 10: 3611
    • 1h Hof F, Schutz A, Fah C, Meyer S, Bur D, Liu J, Goldberg DE, Diederich E. Angew. Chem. Int. Ed. 2006; 45: 2138
    • 2a Frankel BA, Bentley M, Kruger RG, McCafferty DG. J. Am. Chem. Soc. 2004; 126: 3404
    • 2b Kudryavtsev KV, Bentley ML, McCafferty DG. Bioorg. Med. Chem. 2009; 17: 2886
    • 3a Singh A, Rosenthal PJ. J. Biol. Chem. 2004; 279: 35236
    • 3b Palmer JT, Rasnick D, Klaus JL, Bromme D. J. Med. Chem. 1995; 38: 3193
    • 3c Roush WR, Gwaltney II SL, Cheng J, Scheidt KA, Mckerrow JH, Hansell E. J. Am. Chem. Soc. 1998; 120: 10994
  • 4 Liu S, Zhou B, Yang H, He Y, Jiang Z.-X, Kumar S, Wu L, Zhang Z.-Y. J. Am. Chem. Soc. 2008; 130: 8251

    • For representative examples and reviews, see:
    • 5a Supuran CT, Casini A, Scozzafava A. Med. Res. Rev. 2003; 23: 535
    • 5b Meadows DC, Gervay-Hague J. Med. Res. Rev. 2006; 26: 793
    • 5c Ohnuma T, Hata N, Fujiwara H, Ban Y. J. Org. Chem. 1982; 47: 4713
    • 5d Vollhardt J, Gais HJ, Lukas KL. Angew. Chem., Int. Ed. Engl. 1985; 24: 610
    • 5e Qian H, Huang X. Synlett 2001; 1913
    • 5f Huang X, Duan D, Zheng W. J. Org. Chem. 2003; 68: 1958
    • 5g Xu WM, Tang E, Huang X. Synthesis 2004; 2094
    • 5h Cacchi S, Fabrizi G, Goggiamani A, Parisi LM, Bernini R. J. Org. Chem. 2004; 69: 5608
    • 5i Díez D, García P, Marcos IS, Garrido NM, Basabe P, Broughton HB, Howard BB, Urones JG. Tetrahedron 2005; 61: 699
    • 5j Guo H, Zheng Z, Yu F, Ma S, Holuigue A, Tromp DS, Elsevier CJ, Yu Y. Angew. Chem. Int. Ed. 2006; 45: 4997
    • 5k Signore G, Malanga C, Menicagli R. Tetrahedron 2008; 64: 11218
    • 6a Baskin JM, Wang Z. Org. Lett. 2002; 4: 4423
    • 6b Zhu W, Ma D. J. Org. Chem. 2005; 70: 2696
    • 6c Bian M, Xu F, Ma C. Synthesis 2007; 2951
  • 7 Reeves DC, Rodriguez S, Lee H, Hahhad N, Krishnamurthy D, Senanayake CH. Tetrahedron Lett. 2009; 50: 2870
  • 8 Cacchi S, Fabrizi G, Goggiamani A, Parisi LM, Bernini R. J. Org. Chem. 2004; 69: 5608
  • 9 Huang F, Batey RA. Tetrahedron 2007; 63: 7667
    • 10a Nair V, Augustine A, George TG, Nair LG. Tetrahedron Lett. 2001; 42: 6763
    • 10b Nobukazu T. Tetrahedron 2014; 70: 1984
    • 11a Li X.-Q, Xu X.-S, Zhou C. Chem. Commun. 2012; 48: 12240
    • 11b Li X.-W, Xu Y.-L, Wu W.-Q, Jiang C, Qi C.-R, Jiang H.-F. Chem. Eur. J. 2014; 20: 7911
    • 11c Tang S, Wu Y, Liao W.-Q, Bai R.-P, Liu C, Lei A.-W. Chem. Commun. 2014; 50: 4496
    • 11d Li X.-Q, Shi X.-H, Fang M.-W, Xu X.-S. J. Org. Chem. 2013; 78: 9499
    • 11e Rong G.-W, Mao J.-C, Yan H, Zheng Y, Zhang G.-Q. J. Org. Chem. 2015; 80: 4697
    • 11f Li S.-Y, Li X, Yang F, Wu Y.-J. Org. Chem. Front. 2015; 2: 1076
    • 12a Hao L, Wu F, Ding Z.-C, Xu S.-X, Ma Y.-L, Zhan Z.-P. Chem. Eur. J. 2012; 18: 6453
    • 12b Xu S.-X, Hao L, Wang T, Ding Z.-C, Zhan Z.-P. Org. Biomol. Chem. 2013; 11: 294
    • 12c Hao L, Hong J.-J, Zhu J, Zhan Z.-P. Chem. Eur. J. 2013; 19: 5715
    • 12d Zhu Y, Tang H.-T, Zhan Z.-P. Adv. Synth. Catal. 2013; 355: 1291
    • 12e Zhu Y, Lu W.-T, Sun H.-C, Zhan Z.-P. Org. Lett. 2013; 15: 4146
    • 12f Wen J.-J, Tang H.-T, Xiong K, Ding Z.-C, Zhan Z.-P. Org. Lett. 2014; 16: 5940
    • 12g Tang H.-T, Xiong K, Li R.-H, Ding Z.-C, Zhan Z.-P. Org. Lett. 2015; 17: 326
    • 12h Ding Z.-C, Tang H.-T, Li R.-H, Ju L.-C, Zhan Z.-P. J. Org. Chem. 2015; 80: 9307
    • 12i Li R.-H, Ding C.-K, Jiang Y.-N, Ding Z.-C, An X.-M, Tang H.-T, Jing Q.-W, Zhan Z.-P. Org. Lett. 2016; 18: 1666
  • 13 Liu X.-Y, Duan X.-H, Pan Z.-L, Han Y, Liang Y.-M. Synlett 2005; 1752
  • 14 Chen Z.-K, Yan Q.-Q, Liu Z.-X, Xu Y.-M, Zhang Y.-H. Angew. Chem. Int. Ed. 2013; 52: 13324