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Synthesis 2018; 50(11): 2231-2234
DOI: 10.1055/s-0037-1609446
DOI: 10.1055/s-0037-1609446
paper
An Efficient Oxidation of Sulfides to Sulfones with Urea–Hydrogen Peroxide in the Presence of Phthalic Anhydride in Ethyl Acetate
This work was supported by Regis Technologies, Inc.Further Information
Publication History
Received: 27 February 2018
Accepted after revision: 14 March 2018
Publication Date:
04 April 2018 (online)

Abstract
A metal-free, environmentally benign oxidation of substituted sulfides directly to their corresponding sulfones is described. Using urea-hydrogen peroxide and phthalic anhydride in ethyl acetate clean conversion into the sulfone was achieved without observation of the possible sulfoxide oxidation product.
Key words
sulfones - sulfoxides - sulfide oxidation - urea–hydrogen peroxide - UHP - phthalic anhydrideSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1609446.
- Supporting Information
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References
- 1 Feng M. Tang B. Liang SH. Jiang X. Curr. Top. Med. Chem. 2016; 16: 1200
- 2 Devendar P. Yang G.-F. Top. Curr. Chem. 2017; 375: 82
- 3 Waldman AJ. Ng TL. Wang P. Balskus EP. Chem. Rev. 2017; 117: 5784
- 4 Liu N.-W. Liang S. Manolikakes G. Synthesis 2016; 48: 1939
- 5a Xu L. Cheng J. Trudell ML. J. Org. Chem. 2003; 68: 5388
- 5b Yamazaki S. Bull. Chem. Soc. Jpn. 1996; 69: 2955
- 5c Sato K. Hyodo M. Aoki M. Zheng X.-Q. Noyori R. Tetrahedron 2001; 57: 2469
- 5d Ward RS. Roberts DW. Diaper RL. Sulfur Lett. 2000; 23: 139
- 5e Leonard NJ. Johnson CR. J. Org. Chem. 1962; 27: 282
- 5f Varma RS. Saini RK. Meshram HM. Tetrahedron Lett. 1997; 38: 6525
- 5g Paquette LA. Carr RV. C. Org. Synth. Coll. 1990; 7: 453
- 5h Gokel GW. Gerdes HM. Dishong DM. J. Org. Chem. 1980; 45: 3634
- 6 Kaczmarek L. Balicki R. Nantka-Namirski P. Chem. Ber. 1992; 125: 1965
- 7 Heaney H. Cardona F. Goti A. Hydrogen Peroxide-Urea: e-EROS Encyclopedia of Reagents for Organic Synthesis . Wiley; New York: 2008
- 8 Cooper MS. Heaney H. Newbold AJ. Sanderson WR. Synlett 1990; 533
- 9 Balicki R. Synth. Commun. 1999; 29: 2235
- 10a Sato K. Hyodo M. Aoki M. Zheng X.-Q. Noyori R. Tetrahedron 2001; 57: 2469
- 10b Karimi B. Ghoreishi-Nezhad M. Clark JH. Org. Lett. 2005; 7: 625
- 11 Balicki R. Kaczmarek L. Nantka-Namirski P. Liebigs Ann. Chem. 1992; 883
- 12 Balicki R. Kaczmarek L. Nantka-Namirski P. J. Prakt. Chem. 1993; 335: 209
- 13 Voutyritsa E. Triandafillidi I. Kokotos CG. Synthesis 2017; 49: 917
- 14 Fukuda N. Ikemoto T. J. Org. Chem. 2010; 75: 4629
- 15 Klemm LH. Porter QN. J. Org. Chem. 1981; 46: 2184
- 16 Crich D. Hutton TK. Ranganathan K. J. Org. Chem. 2005; 70: 7672
- 17 Beaulieu F. Snieckus V. J. Org. Chem. 1994; 59: 6508
- 18 Becker DP. Villamil CI. Barta TE. Bedell LJ. Boehm TL. DeCrescenzo GA. Freskos JN. Getman DP. Hockerman S. Heintz R. Howard SC. Li MH. McDonald JJ. Carron CP. Funckes-Shippy CL. Mehta PP. Munie GE. Swearingen CA. J. Med. Chem. 2005; 48: 6713