A Mild and Highly Efficient Oxidation of Sulfides to Sulfoxides with Periodic Acid Catalyzed by FeCl3

Sung Soo  Kim; Kasi  Nehru; Sang Soo  Kim; Dong Won  Kim; Hyun Chul  Jung

doi:10.1055/s-2002-35623

SHORTPAPER

A Mild and Highly Efficient Oxidation of Sulfides to Sulfoxides with Periodic Acid Catalyzed by FeCl₃

Sung Soo Kim*, Kasi Nehru, Sang Soo Kim, Dong Won Kim, Hyun Chul Jung
Department of Chemistry and Center for Chemical Dynamics, Inha University, Incheon 402-751, South Korea
Fax: +82(32)8675604; e-Mail: sungsoo@inha.ac.kr;

Abstract

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Abstract

An excellent method for the selective oxidation of sulfides to sulfoxides with periodic acid (H₅IO₆) catalyzed by FeCl₃ in MeCN has been devised. The reported procedure is fast, simple and the yields are excellent (>98%) in most cases with reaction time of less than 2 minutes.

Key words

sulfides - sulfoxides - periodic acid - iron chloride - hypervalent

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References

1

Dr. Kasi Nehru is a visiting scholar from Madurai Kamaraj University on a grant from BK 21(2001).

2a Hollingworth GJ. In Comprehensive Organic Functional Group Transformations Vol. 2: Katritzky AR. Meth-Cohn O. Rees CW. Pattenden G. Elsevier; Oxford: 1995.

2b The Synthesis of Sulfones, Sulfoxides and Cyclic Sulfides Patai S. Rappoport Z. Wiley; New York: 1994.

3 Ravikumar KS. Bégué J.-P. Bonnet-Delpon D. Tetrahedron Lett. 1998, 39: 3141

4 Gasparrini F. Giovannoli M. Misiti D. J. Org. Chem. 1990, 55: 1323

5 Roh KR. Kim KS. Kim YH. Tetrahedron Lett. 1991, 32: 793

6 Orito K. Hatakeyama T. Takeo M. Suginome H. Synthesis 1995, 1357 ; and references therein

7 Arterburn JB. Nelson SL. J. Org. Chem. 1996, 61: 2260

8 Bonadies F. Angelis FD. Locati L. Scettri A. Tetrahedron Lett. 1996, 37: 7129

9 Sevvel R. Rajagopal S. Srinivasan C. Alhaji NI. Chellamani A. J. Org. Chem. 2000, 65: 3334

10 Pautet F. Daudon M. Tetrahedron Lett. 1991, 32: 1457

11 Ali MH. Stevens WC. Synthesis 1997, 764 ; and references cited therein

12 Ali MH. Bohnert GJ. Synthesis 1998, 1238

13a Breton GW. Fields JD. Kropp PJ. Tetrahedron Lett. 1995, 36: 3825

13b Kropp PJ. Breton GW. Fields JD. Tung JC. Loomis BR. J. Am. Chem. Soc. 2000, 122: 4280

14 Hirano M. Yakabe S. Itoh S. Clark JH. Morimotoa T. Synthesis 1997, 1161 ; and references cited therein

15a Varvoglis A. Hypervalent Iodine in Organic Synthesis Academic Press; San Diego: 1997.

15b Stang PJ. Zhdankin VV. Chem. Rev. 1996, 96: 1123

16 Srinivasan C. Chellamani A. Kuthalingam P. J. Org. Chem. 1982, 47: 428

17 Ochiai M. Nakanishi A. Ito T. J. Org. Chem. 1997, 62: 4253

18 Barton DHR. Li W. Smith JA. Tetrahedron Lett. 1998, 39: 7055

19 Tohma H. Takizawa S. Watanabe H. Fukuoka Y. Maegawa T. Kita Y. J. Org. Chem. 1999, 64: 3519

20 Kim SS. Nehru K. Synlett 2002, 616

21 Murray RW. Jeyaraman R. Pillay MK. J. Org. Chem. 1987, 52: 746

22 Pouchert CJ. Behnke J. The Aldrich Library of ¹³C and ¹H FT NMR Spectra 1st ed., Vol.2: Aldrich; USA: 1993.

23 Oae BS. Ohnishi Y. Kozuka S. Tagaki W. Bull. Chem. Soc. Jpn. 1966, 39: 364

24 Hojo M. Yoshida Z. J. Am. Chem. Soc. 1968, 90: 4496

25 Liu K.-T. Tong Y.-C. J. Org. Chem. 1978, 43: 2717