Mild and Efficient Deoxygenation
of Sulfoxides to Sulfides with Triflic Anhydride/Potassium
Iodide Reagent System

Kiumars Bahrami; Mohammad Mehdi Khodaei; Ahmad Karimi

doi:10.1055/s-2008-1067190

PAPER

Mild and Efficient Deoxygenation of Sulfoxides to Sulfides with Triflic Anhydride/Potassium Iodide Reagent System

Kiumars Bahrami*^a,b, Mohammad Mehdi Khodaei*^a,b, Ahmad Karimi^a
^a Department of Chemistry, Razi University, Kermanshah 67149, Iran
^b Nanoscience and Nanotechnology Research Center (NNRC), Razi University, Kermanshah 67149, Iran
Fax: +98(831)4274559; e-Mail: kbahrami2@hotmail.com; e-Mail: mmkhoda@razi.ac.ir;

Abstract

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Abstract

It was found that the combination of triflic anhydride/potassium iodide was an effective promoter for the deoxygenation of sulfoxides and gave the corresponding sulfides in excellent yield in acetonitrile at room temperature. It is worth mentioning that this reagent system is chemoselective and tolerates various functional groups, such as alkene, ketone, ester, aldehyde, acid, and oxime.

Key words

deoxygenation - sulfoxide - sulfide - chemoselective - triflic anhydride

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References

<A NAME="RZ08808SS-1">1</A> Black S. Harte EM. Hudson B. Wartofsky L. J. Biol. Chem. 1960, 235: 2910

<A NAME="RZ08808SS-2A">2a</A> Khurana JM. Ray A. Singh S. Tetrahedron Lett. 1998, 39: 3829

<A NAME="RZ08808SS-2B">2b</A> Karimi B. Zareyee D. Synthesis 2003, 1875

<A NAME="RZ08808SS-2C">2c</A> Iranpoor N. Firouzabadi H. Shaterian HR. J. Org. Chem. 2002, 67: 2826

<A NAME="RZ08808SS-2D">2d</A> Karimi B. Zareyee D. Synthesis 2003, 335

<A NAME="RZ08808SS-2E">2e</A> Posner GH. Tang PW. J. Org. Chem. 1978, 43: 4131

<A NAME="RZ08808SS-2F">2f</A> Madesclaire M. Tetrahedron 1988, 44: 6537

<A NAME="RZ08808SS-3A">3a</A> Firouzabadi H. Karimi B. Synthesis 1999, 500

<A NAME="RZ08808SS-3B">3b</A> Yoo B. Choi KH. Kim DY. Choi KI. Kim JH. Synth. Commun. 2003, 33: 53

<A NAME="RZ08808SS-3C">3c</A> Miller SJ. Collier TR. Wu W. Tetrahedron Lett. 2000, 41: 3781

<A NAME="RZ08808SS-4A">4a</A> Szmant HH. Cox O. J. Org. Chem. 1966, 31: 1595

<A NAME="RZ08808SS-4B">4b</A> Kikuchi S. Konishi H. Hashimoto Y. Tetrahedron 2005, 61: 3587

<A NAME="RZ08808SS-4C">4c</A> Kikuchi S. Hashimoto Y. Synlett 2004, 1267

<A NAME="RZ08808SS-4D">4d</A> Hashimoto Y. Konishi H. Kikuchi S. Synlett 2004, 1264

<A NAME="RZ08808SS-4E">4e</A> Hashimoto Y. Kikuchi S. Chem. Lett. 2002, 126

<A NAME="RZ08808SS-5A">5a</A> Harrison DJ. Tam NC. Vogels CM. Langler RF. Baker RT. Decken A. Westcott SA. Tetrahedron Lett. 2004, 45: 8493

<A NAME="RZ08808SS-5B">5b</A> Palazzi C. Colombo L. Gennari C. Tetrahedron Lett. 1986, 27: 1735

<A NAME="RZ08808SS-5C">5c</A> Suzuki I. Yamamoto Y. J. Org. Chem. 1993, 58: 4783

<A NAME="RZ08808SS-5D">5d</A> Shi M. Jiang JK. Cui SC. Feng YS. J. Chem. Soc., Perkin Trans. 1 2001, 390

<A NAME="RZ08808SS-6">6</A> Bahrami K. Khodaei MM. Khedri M. Chem. Lett. 2007, 36: 1324

<A NAME="RZ08808SS-7A">7a</A> Khodaei MM. Alizade AA. Nazari M. Tetrahedron Lett. 2007, 48: 4199

<A NAME="RZ08808SS-7B">7b</A> Alizade AA. Khodaei MM. Nazari M. Tetrahedron Lett. 2007, 48: 6805

<A NAME="RZ08808SS-8A">8a</A> Khurana JM. Sharma V. Chacko SA. Tetrahedron 2007, 63: 966

<A NAME="RZ08808SS-8B">8b</A> Hua G. Woolins JD. Tetrahedron Lett. 2007, 48: 3677

<A NAME="RZ08808SS-8C">8c</A> Snyde HR. Handrick GR. J. Am. Chem. Soc. 1944, 66: 1860

<A NAME="RZ08808SS-8D">8d</A> Clark NG. Cranham JE. Greenwood D. Marshall JR. Stevenson HA. J. Sci. Food Agric. 1957, 8: 566

<A NAME="RZ08808SS-9A">9a</A> Brookes RF. Clark NG. Cranham JE. Greenwood D. Marshall JR. Stevenson HA. J. Sci. Food Agric. 1958, 9: 111

<A NAME="RZ08808SS-9B">9b</A> Brookes RF. Cranham JE. Greenwood D. Stevenson HA. J. Sci. Food Agric. 1958, 9: 141

<A NAME="RZ08808SS-9C">9c</A> Coulon E. Pinson J. J. Org. Chem. 2002, 67: 8513

<A NAME="RZ08808SS-9D">9d</A> Rossi RA. Palacios SM. J. Org. Chem. 1981, 46: 5300

<A NAME="RZ08808SS-10A">10a</A> Wladislaw B. Olivato PR. Sala O. J. Chem. Soc. B 1971, 2037

<A NAME="RZ08808SS-10B">10b</A> Hiskey RG. Carroll FI. J. Am. Chem. Soc. 1961, 83: 4647

<A NAME="RZ08808SS-10C">10c</A> Kim JK. Caserio MC. J. Org. Chem. 1979, 44: 1897

<A NAME="RZ08808SS-10D">10d</A> Nishimura H. Mizutani J. J. Org. Chem. 1975, 40: 1567

<A NAME="RZ08808SS-10E">10e</A> D. Chasar W. Shockcor JP. Phosphorus, Sulfur Relat. Elem. 1980, 8: 187

<A NAME="RZ08808SS-11">11</A> Jitender MK. Abhijit R. Sarika S. Tetrahedron Lett. 1998, 39: 3829

<A NAME="RZ08808SS-12">12</A> Ana CF. Carlos CR. Tetrahedron 2006, 62: 9650

<A NAME="RZ08808SS-13">13</A> Samantha JM. Talia RC. Weiming W. Tetrahedron Lett. 2000, 41: 3781

<A NAME="RZ08808SS-14">14</A> Kikuchi S. Konishi H. Hashimoto Y. Tetrahedron 2005, 61: 3587

<A NAME="RZ08808SS-15">15</A> Shimizu M. Shibuya K. Hayakawa R. Synlett 2000, 1437

<A NAME="RZ08808SS-16">16</A> Vankar YD. Rao CT. Tetrahedron Lett. 1985, 26: 2717

<A NAME="RZ08808SS-17">17</A> Guindon Y. Atkinson JG. Morton HE. J. Org. Chem. 1984, 49: 4538