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

Zhanhui Yang; Bingnan Zhou; Jiaxi Xu

doi:10.1055/s-0033-1338567

Synthesis, Inhaltsverzeichnis

Synthesis 2014; 46(02): 225-229
DOI: 10.1055/s-0033-1338567

paper

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

Autoren

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

Abstract

Alle Artikel dieser Rubrik

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%.

Key words

bleach - sulfonyl chloride - S-alkyl isothiourea - chlorosulfonation - oxidation

Volltext

Referenzen

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

Zusatzmaterial

Supporting Information (PDF) (opens in new window)