Synthesis 2014; 46(02): 225-229
DOI: 10.1055/s-0033-1338567
paper
© Georg Thieme Verlag Stuttgart · New York

Clean and Economic Synthesis of Alkanesulfonyl Chlorides from S-Alkyl Isothiourea Salts via Bleach Oxidative Chlorosulfonation

Zhanhui Yang
State Key Laboratory of Chemical Resource Engineering, Department of Organic Chemistry, Faculty of Science, Beijing University of Chemical Technology, Beijing 100029, P. R. of China   Fax: +86(10)64435565   eMail: jxxu@mail.buct.edu.cn
,
Bingnan Zhou
State Key Laboratory of Chemical Resource Engineering, Department of Organic Chemistry, Faculty of Science, Beijing University of Chemical Technology, Beijing 100029, P. R. of China   Fax: +86(10)64435565   eMail: jxxu@mail.buct.edu.cn
,
Jiaxi Xu*
State Key Laboratory of Chemical Resource Engineering, Department of Organic Chemistry, Faculty of Science, Beijing University of Chemical Technology, Beijing 100029, P. R. of China   Fax: +86(10)64435565   eMail: jxxu@mail.buct.edu.cn
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Publikationsverlauf

Received: 11. Oktober 2013

Accepted after revision: 08. November 2013

Publikationsdatum:
28. November 2013 (online)


Abstract

A simple procedure for clean and economic synthesis of alkanesulfonyl chlorides via bleach-mediated oxidative chlorosulfonation of S-alkyl isothiourea salts is disclosed. This procedure is environment- and worker-friendly with the advantages of readily accessible materials and reagents, simple and safe operations, easy purification without chromatography, and affords high yields of up to 99%.

Supporting Information

 
  • References

    • 1a Opitz G. Angew. Chem., Int. Ed. Engl. 1967; 6: 107
    • 1b King JF. Acc. Chem. Res. 1975; 8: 10
    • 1c Williams A, Douglas KT. Chem. Rev. 1975; 75: 627

    • For recent examples, see:
    • 1d Zajac M, Peters R. Org. Lett. 2007; 9: 2007
    • 1e Koch FM, Peters R. Angew. Chem. Int. Ed. 2007; 46: 2685
    • 1f He FD, Meng FH, Song XQ, Hu WX, Xu JX. Org. Lett. 2009; 11: 3922
    • 2a Monnee MC. F, Marijne MF, Brouwer AJ, Liskamp RM. J. Tetrahedron Lett. 2000; 41: 7991
    • 2b Piatek A, Chapuis C, Jurczak J. Helv. Chim. Acta 2002; 85: 1973
    • 2c Humljan J, Gobec S. Tetrahedron Lett. 2005; 46: 4069
    • 2d Bahrami K, Khodaei MM, Soheilizad M. J. Org. Chem. 2009; 74: 9287
    • 2e Kværnø L, Werder M, Hauser H, Carreira EM. Org. Lett. 2005; 7: 1145
    • 2f Park YJ, Shin HH, Kim YH. Chem. Lett. 1992; 1483
    • 2g Meinzer A, Breckel A, Thaher BA, Manicone N, Otto H.-H. Helv. Chim. Acta 2004; 87: 90
    • 2h Kim DW, Ko YK, Kim SH. Synthesis 1992; 1203
    • 2i Nishiguchi A, Maeda K, Miki S. Synthesis 2006; 4131
    • 2j Liu J, Hou SL, Xu JX. Phosphorus Sulfur Silicon Relat. Elem. 2011; 186: 2377
    • 2k Meng FH, Chen N, Xu JX. Sci. China Chem. 2012; 55: 2548 ; Chem. Abstr. 2012, 158, 272601
    • 2l Surya PrakashG. K, Mathew T, Panja C, Olah GA. J. Org. Chem. 2007; 72: 5847
    • 2m Massah AR, Sayadi S, Ebrahimi S. RSC Adv. 2012; 2: 6606
    • 2n Joyard Y, Papamicael C, Bohn P, Bischoff L. Org. Lett. 2013; 15: 2294
    • 2o Pu Y.-M, Christesen A, Ku Y.-Y. Tetrahedron Lett. 2010; 51: 418
    • 3a Johnson TB, Sprague JM. J. Am. Chem. Soc. 1936; 58: 1348
    • 3b Sprague JM, Johnson TB. J. Am. Chem. Soc. 1937; 59: 1837
    • 3c Dang Z, Kang R. Chin. J. Appl. Chem. 1995; 12: 103 ; Chem. Abstr. 1995, 122, 190980
    • 3d Dang Z, Kang R, Wu R, Zhang L. Chem. Reagents (Beijing, China) 1995; 17: 165 ; Chem. Abstr. 1995, 123, 198248
    • 3e Zhen X, Kang R, Han J. Huaxue Tongbao 1996; 37 ; Chem. Abstr. 1996, 125, 167302
    • 3f Sohmiya H, Kimura T, Fujita M, Ando T. Chem. Lett. 1992; 891
    • 3g Sohmiya H, Kimura T, Fujita M, Ando T. Tetrahedron 1998; 54: 13737
    • 3h Yang ZH, Xu JX. Synthesis 2013; 45: 1675
    • 3i Bonk JD, Dellaria Jr JF. PCT Int. Appl. WO 2005066169, 2005 ; Chem. Abstr. 2005, 143, 153375.
    • 3j Yang ZH, Zheng YP, Xu JX. Synlett 2013; 24: 2165
    • 4a Wright SW, Hallstrom KN. J. Org. Chem. 2006; 71: 1080
    • 4b Aleksandrovich SE, Anatol’evich SP, Leonidovna KA. Russian Patent 2400474, 2010 ; Chem. Abstr. 2010, 153, 456203.
    • 5a Hughes TV, Hammond SD, Cava MP. J. Org. Chem. 1998; 63: 401
    • 5b Kim J.-J, Kweon D-H, Cho S-D, Kim H.-K, Lee S.-G, Yoon Y.-J. Synlett 2006; 194
    • 5c Barker TJ, Jarvo ER. J. Am. Chem. Soc. 2009; 131: 15598
    • 6a Krishnan S, Kuhn DG, Hamilton GA. J. Am. Chem. Soc. 1977; 99: 8121
    • 6b Reamonn LS, O’Sullivan WI. J. Chem. Soc., Chem. Commun. 1976; 1012
    • 6c Fonouni HE, Krishnan S, Kuhn DG, Hamilton GA. J. Am. Chem. Soc. 1983; 105: 7622
    • 6d Meunier B, Guilmet E, De Carvalbo ME, Poilblanc R. J. Am. Chem. Soc. 1984; 106: 6668
    • 6e Yoon H, Burrows CJ. J. Am. Chem. Soc. 1988; 110: 4087
    • 6f Dettwiler JE, Lubell WD. J. Org. Chem. 2003; 68: 177
    • 6g Gonsalvi L, Arends IW. C. E, Moilanen P, Sheldon RA. Adv. Synth. Catal. 2003; 345: 1321
    • 6h Gonsalvi L, Arends IW. C. E, Sheldon RA. Org. Lett. 2002; 4: 1659
  • 7 Alfonsi K, Colberg J, Dunn PJ, Fevig T, Jennings S, Johnson TA, Kleine HP, Knight C, Nagy MA, Perry DA, Stefaniak M. Green Chem. 2008; 10: 31

    • For selected examples see:
    • 8a Optiz G, Fischer K. Angew. Chem., Int. Ed. Engl. 1965; 4: 41
    • 8b King JF, Durst T. Can. J. Chem. 1966; 44: 819
    • 8c Truce WE, Abraham DJ, Son P. J. Org. Chem. 1967; 32: 990

      For selected examples, see:
    • 9a McKew JC, Lee KL, Shen MW. H, Thakker P, Foley MA, Behnke ML, Hu B, Sum F.-W, Tam S, Hu Y, Chen L, Kirincich SJ, Michalak R, Thomason J, Ipek M, Wu K, Wooder L, Ramarao MK, Murphy EA, Goodwin DG, Albert L, Xu X, Donahue F, Ku MS, Keith J, Nickerson-Nutter CL, Abraham WM, Williams C, Hegen M, Clark JD. J. Med. Chem. 2008; 51: 3388
    • 9b McKew JC, Lee KL, Chen L, Vargas R, Clark JD, Williams C, Clerin V, Marusic S, Pong K. PCT Int. Appl. WO 2006128142, 2006 ; Chem. Abstr. 2006, 142, 27723.
    • 9c Ting PC, Aslanian RG, Cao J, Kim DW.-S, Kuang R, Zhou G, Herr RJ, Zych AJ, Yang J, Wu H, Zorn N. PTC Int. Appl. WO 2008115381, 2008 ; Chem. Abstr. 2008, 149, 402395.
    • 10a Hoyle J In The Chemistry of Sulfonic Acids, Esters and Their Derivatives . Patai S, Rapport Z. Wiley; New York: 1991. Chap. 10, 351
    • 10b Tanaka K In The Chemistry of Sulfonic Acids, Esters and Their Derivatives . Patai S, Rapport Z. Wiley; New York: 1991. Chap. 11, 401
    • 11a Synthesis of 3o: Jüschke R, Velayutham D, Sartori P. J. Fluorine Chem. 1997; 83: 145
    • 11b Synthesis of 3p: Shinohara A, Hasegawa N, Kawasumi M, Takami M, Yoshida T. PCT Int. Appl. WO 2011144992, 2011 ; Chem. Abstr. 2011, 155, 684742.

      Use of 3o:
    • 12a Goerdeler J, Ullmann H. Chem. Ber. 1961; 94: 1067
    • 12b Ogura F, Yamaguchi H, Otsubo T, Nakano T, Saito T. Bull. Chem. Soc. Jpn. 1983; 56: 1257
    • 12c Herkelmann R, Sartori P. J. Fluorine Chem. 1989; 44: 299
    • 12d Kong X, Levens N, Bouzide A, Ciblat S, Frenette R, Renaud J. PCT Int. Appl. WO 2011017800, 2011 ; Chem. Abstr. 2011, 154, 259094.

    • Use of 3p:
    • 12e Beachem MT, Shaw JT, Sargent GD, Fortenbaugh RB, Salsbury JM. J. Am. Chem. Soc. 1959; 81: 5430
    • 12f Panov EP, Kostyuchenko VM, Skrypnik YG, Zolotukhin SP, Vizgert RV. Zh. Org. Khim. 1976; 12: 824 ; Chem. Abstr. 1976, 85, 4820
    • 12g Gustinya DV, Markava E, Liepins E, Freimanis J. Zh. Org. Khim. 1989; 25: 143 ; Chem. Abstr. 1989, 111, 114659
    • 12h Griesgraber GW. PCT Int. Appl. WO 2004028539, 2004 ; Chem. Abstr. 2004, 140, 321358.
  • 13 Miller E. J. Am. Chem. Soc. 1940; 62: 2099
  • 14 Johnston TP. J. Org. Chem. 1960; 25: 399