Synthesis of diaryl disulfides via the reductive coupling of arylsulfonyl chlorides

Tetrahedron Letters

Volumn 50, Issue 52, 2009, Pages 7340-7342

  Kabalka, George W ^a   Reddy, Marepally Srinivasa ^a   Yao, Min Liang ^a  

^a UNIVERSITY OF TENNESSEE   (United States)

Author keywords

Arylsulfonyl chloride; Coupling; Disulfide; Triphenylphosphine

Indexed keywords

ARYLSULFONYL CHLORIDE; CHLORIDE; DIARYL DISULFIDE; DISULFIDE; TRIPHENYLPHOSPHINE; UNCLASSIFIED DRUG;

ARTICLE; MODEL; REDUCTION; ROOM TEMPERATURE; SYNTHESIS;

EID: 70449091869     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.10.061     Document Type: Article

References (37)

1. Arisawa M., Fujimoto K., Morinaka S., and Yamaguchi M. J. Am. Chem. Soc. 127 (2005) 12226
2. Nishiyama Y., Kawamatsu H., and Sonoda N. J. Org. Chem. 70 (2005) 2551
3. Ferris K.F., and Franz J.A. J. Org. Chem. 57 (1992) 777
4. Antebi S., and Alper H. Tetrahedron Lett. 26 (1985) 2609
5. Ogawa A., Nishiyama Y., Kambe N., Murai S., and Sonoda N. Tetrahedron Lett. 28 (1987) 3271
6. Rice W.G., Turpin J.A., Schaeffer C.A., Graham L., Clanton D., Buckheit Jr. R.W., Zaharevitz D., Summers M.F., Wallqvist A., and Covell D.G. J. Med. Chem. 39 (1996) 3606
7. Dougherty G., and Haas O. J. Am. Chem. Soc. 59 (1937) 2469
8. Kuhle E. The Chemistry of the Sulfenic Acids (1973), Georg Thieme, Stuttgart
9. Douglass I.B., and Norton R.V. J. Org. Chem. 33 (1968) 2104
10. Douglass I.B. J. Org. Chem. 39 (1974) 563
11. Leino R., and Lönnqvist J.-E. Tetrahedron Lett. 45 (2004) 8489
12. Carril M., SanMartin R., Domínguez E., and Tellitu I. Green Chem. 3 (2007) 315 and references cited therein
13. Oae S., and ToGo H. Bull. Chem. Soc. Jpn. 56 (1983) 3813
14. Oae S., and ToGo H. Bull. Chem. Soc. Jpn. 56 (1983) 3802
15. Suzuki H., Tani H., and Osuka A. Chem. Lett. (1984) 139
16. Suter C.M. The Organic Chemistry of Sulfur (1969), Intrascience Research Foundation, Santa Monica, CA
17. Iranpoor N., Firouzabadi H., and Jamalian A. Synlett (2005) 1447
18. Liua Y., and Zhang Y. Tetrahedron Lett. 44 (2003) 4291
19. Guo H., Wang J., and Zhang Y. Synth. Commun. 27 (1997) 85
20. Dhar P., Ranjan R., and Chandrasekaran S. J. Org. Chem. 55 (1990) 3728
21. Bauer L., and Cymerman J. J. Chem. Soc. (1949) 3434
22. Alper H. Angew. Chem., Int. Ed. Engl. 81 (1969) 706
23. Firouzabadi H., and Karimi B. Synthesis (1999) 500
24. Olah G.A., Narang S.C., Field L.D., and Salem G.F. J. Org. Chem. 45 (1980) 4792
25. Kielbasinski P., Drabowicz J., and Mikolajczyk M. J. Org. Chem. 47 (1982) 4808
26. Chan T.H., Montillier J.P., Vanhorn W.H., and Harpp D.N. J. Am. Chem. Soc. 92 (1970) 7224
27. Babu R.J., and Bhatt V.M. Tetrahedron Lett. 27 (1986) 1073
28. Narayana C., Padmanabhan S., and Kabalka G.W. Synlett. (1991) 125
29. Fujimori K., Togo H., and Oae S. Tetrahedron Lett. 21 (1980) 4921
30. To remove a trace amount of sulfonic acid, para-toluenesulfonyl chloride was recrystalized from hexanes prior to use.
31. Typical reaction procedure: To a solution of para-toluenesulfonyl chloride (190 mg, 1.0 mmol) in tetrahydrofuran (5 mL) was added triphenylphosphine (524 mg, 2.0 mmol). The mixture was stirred at room temperature and monitored by TLC. After completion of the reaction, the solvent was removed under reduced pressure and the residue was dissolved in a minimum amount of ethyl acetate (4 mL). To this solution, hexane was added dropwise (about 30 mL) and the byproduct triphenylphosphine oxide was precipitated and was removed by filtration. Concentration of the filtrate under reduced pressure and silica gel column chromatography using hexane as eluant yielded the desired product (114 mg, 92% yield).
32. Masaki M., Fukui K., and Kita J. Bull. Chem. Soc. Jpn. 50 (1977) 2013
33. Wittig G., and Schöllkopf U. Chem. Ber. 87 (1954) 1318
34. Mitsunobu O., and Yamada Y. Bull. Chem. Soc. Jpn. 40 (1967) 2380
35. Appel R. Angew. Chem., Int. Ed. Engl. 14 (1975) 801
36. Douglass I.B., Norton R.V., Weichman R.L., and Clarkson R.B. J. Org. Chem. 34 (1969) 1803
37. The light yellow color of the reaction mixtures suggests that chlorine may be a byproduct. However, attempts to detect chlorine using wet KI-Starch paper were unsuccessful.