Iodine-Mediated α-Sulfonyloxylation of Alkyl Aryl Ketones with Oxone® and Sulfonic Acids

Hiroki Kikui; Katsuhiko Moriyama; Hideo Togo

doi:10.1055/s-0032-1318199

Synthesis, Table of Contents

Synthesis 2013; 45(6): 791-797
DOI: 10.1055/s-0032-1318199

paper

Iodine-Mediated α-Sulfonyloxylation of Alkyl Aryl Ketones with Oxone^® and Sulfonic Acids

Authors

Hiroki Kikui

Graduate School of Science, Chiba University, Yayoi-cho 1-33, Inage-ku, Chiba 263-8522, Japan Email: togo@faculty.chiba-u.jp
Katsuhiko Moriyama

Graduate School of Science, Chiba University, Yayoi-cho 1-33, Inage-ku, Chiba 263-8522, Japan Email: togo@faculty.chiba-u.jp
Hideo Togo*

Graduate School of Science, Chiba University, Yayoi-cho 1-33, Inage-ku, Chiba 263-8522, Japan Email: togo@faculty.chiba-u.jp

Abstract

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Abstract

Alkyl aryl ketones are converted into the corresponding α-sulfonyloxyketones, in moderate to excellent yields, via a novel procedure that utilizes Oxone^®, p-toluenesulfonic acid or methanesulfonic acid and molecular iodine in a mixture of acetonitrile and 2,2,2-trifluoroethanol. The yield is found to be dependent on the nature of the ketone. A mechanism is proposed in which the key intermediates are an α-iodoketone and a subsequently formed α-iodosylketone. The latter reacts with the sulfonic acid to afford the α-sulfonyloxyketone product.

Key words

α-sulfonyloxyketones - Oxone^® - molecular iodine - p-toluenesulfonic acid - methanesulfonic acid

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References

References

1a Review: Moriarty RM, Vaid RK, Koser GF. Synlett 1990; 365
1b Review: Koser GF. Aldrichimica Acta 2001; 34: 89
1c Prakash O, Saini N, Sharma PK. Heterocycles 1994; 38: 409
1d Neilands O, Karele B. J. Org. Chem. USSR 1970; 6: 885
1e Koser GF, Wettach RH, Troup JM, Frenz BA. J. Org. Chem. 1976; 41: 3609
1f Koser GF, Wettach RH. J. Org. Chem. 1977; 42: 1476
1g Koser GF, Wettach RH, Smith CS. J. Org. Chem. 1980; 45: 1543
1h Koser GF, Relenyi AG, Kalos AN, Rebrovic L, Wettach RH. J. Org. Chem. 1982; 47: 2487
1i Moriarty RM, Penmasta R, Awasthi AK, Epa WR, Prakash I. J. Org. Chem. 1989; 54: 1101
1j Moriarty RM, Vaid RK, Hopkins TE, Vaid BK, Prakash O. Tetrahedron Lett. 1990; 31: 201
1k Tuncay A, Dustman JA, Fisher G, Tuncay CI. Tetrahedron Lett. 1992; 33: 7647
1l Moriarty RM, Vaid BK, Duncan MP, Levy SG, Prakash O, Goyal S. Synthesis 1992; 845
1m Prakash O, Goyal S. Synthesis 1992; 629
1n Prakash O, Rani N, Goyal S. J. Chem. Soc., Perkin Trans. 1 1992; 707
1o Prakash O, Saini N, Sharma PK. Synlett 1994; 221
1p Vrama RS, Kumar D, Liesen PJ. J. Chem. Soc., Perkin Trans. 1 1998; 4093
1q Lee JC, Choi J.-H. Synlett 2001; 234
1r Lai P, Taylor MS. Synthesis 2010; 1449

Monomer reagents:

2a Muraki T, Togo H, Yokoyama M. J. Org. Chem. 1999; 64: 2883
2b Nabana T, Togo H. J. Org. Chem. 2002; 67: 4362
2c Misu Y, Togo H. Org. Biomol. Chem. 2003; 1: 1342
2d Ueno M, Nabana T, Togo H. J. Org. Chem. 2003; 68: 6424

Polymer reagents:

2e Abe S, Sakuratani K, Togo H. Synlett 2001; 22
2f Abe S, Sakuratani K, Togo H. J. Org. Chem. 2001; 66: 6174
2g Sakuratani K, Togo H. ARKIVOC 2003; (vi): 11
2h Ueno M, Togo H. Synthesis 2004; 2673

3a Review: Ochiai M, Miyamoto K. Eur. J. Org. Chem. 2008; 4229
3b Review: Dohi T, Kita Y. Chem. Commun. 2009; 2073
3c Review: Uyanik M, Ishihara K. Chem. Commun. 2009; 2086
3d Ochiai M, Takeuchi Y, Katayama T, Sueda T, Miyamoto K. J. Am. Chem. Soc. 2005; 127: 12244
3e Dohi T, Maruyama A, Yoshimura M, Morimoto K, Tohma H, Kita Y. Angew. Chem. Int. Ed. 2005; 44: 6193
3f Li J, Chan PW. H, Che C. Org. Lett. 2005; 7: 5801
3g Thottumkara AP, Bowsher MS, Vinod TK. Org. Lett. 2005; 7: 2933
3h Dohi T, Maruyama A, Minamitsuji Y, Takenaga N, Kita Y. Chem. Commun. 2007; 1224
3i Richardson RD, Page TK, Altermann S, Paradine SM, French AN, Wirth T. Synlett 2007; 538
3j Yakura T, Konishi T. Synlett 2007; 765
3k Sheng J, Li X, Tang M, Gao B, Huang G. Synthesis 2007; 1165
3l Chen C, Feng X, Zhang G, Zhao Q, Huang G. Synthesis 2008; 3205
3m Uyanik M, Akakura M, Ishihara K. J. Am. Chem. Soc. 2009; 131: 251
3n Miyamoto K, Sei Y, Yamaguchi K, Ochiai M. J. Am. Chem. Soc. 2009; 131: 1382
3o Ojha LR, Kudugunti S, Maddukuri PP, Kommareddy A, Gunna MR, Dokuparthi P, Gottam HB, Botha KK, Parapati DR, Vinod TK. Synlett 2009; 117
3p Dohi T, Minamitsuji Y, Maruyama A, Hirose S, Kita Y. Org. Lett. 2008; 10: 3559
3q Uyanik M, Fukatsu R, Ishihara K. Org. Lett. 2009; 11: 3470
3r Uyanik M, Yasui T, Ishihara K. Bioorg. Med. Chem. Lett. 2009; 19: 3848
3s Yakura T, Tian Y, Yamauchi Y, Omoto M, Konishi T. Chem. Pharm. Bull. 2009; 57: 252
3t Dohi H, Takenaga N, Fukushima K, Uchiyama T, Kato D, Shiro M, Fujioka H, Kita Y. Chem. Commun. 2010; 46: 7697
3u Zagulyaeva AA, Banek CT, Yusubov MS, Zhdankin VV. Org. Lett. 2010; 12: 4644
3v Thottumkara PP, Vinod TK. Org. Lett. 2010; 12: 5640
3w Miura T, Nakashima K, Tada N, Itoh A. Chem. Commun. 2011; 47: 1875
3x Yu Z, Ju X, Wang J, Yu W. Synthesis 2011; 860

4 Yamamoto Y, Togo H. Synlett 2005; 2486

5a Yamamoto Y, Togo H. Synlett 2006; 798
5b Yamamoto Y, Kawano Y, Toy PH, Togo H. Tetrahedron 2007; 63: 4680
5c Akiike J, Yamamoto Y, Togo H. Synlett 2007; 2168

6a Moroda A, Togo H. Synthesis 2008; 1257
6b Ishiwata Y, Togo H. Tetrahedron Lett. 2009; 50: 5354
6c Suzuki Y, Togo H. Synthesis 2010; 2355

7 Kawano Y, Togo H. Tetrahedron 2009; 65: 6251
8 Ishiwata Y, Togo H. Tetrahedron 2009; 65: 10720
9 Tanaka A, Togo H. Synlett 2009; 3360
10 Tanaka A, Moriyama K, Togo H. Synlett 2011; 1853

11a Review: Togo H, Iida S. Synlett 2006; 2159
11b Review: Togo H. J. Synth. Org. Chem. 2008; 66: 652
11c Mori N, Togo H. Synlett 2004; 880
11d Mori N, Togo H. Synlett 2005; 1456
11e Mori N, Togo H. Tetrahedron 2005; 61: 5915
11f Ishihara M, Togo H. Synlett 2006; 227
11g Iida S, Togo H. Synlett 2006; 2633
11h Ihihara M, Togo H. Tetrahedron 2007; 63: 1474
11i Iida S, Togo H. Tetrahedron 2007; 63: 8274
11j Iida S, Togo H. Synlett 2007; 407
11k Iida S, Togo H. Synlett 2008; 1639
11l Iida S, Ohmura R, Togo H. Tetrahedron 2009; 65: 6257
11m Suzuki Y, Moriyama K, Togo H. Tetrahedron Lett. 2010; 51: 5950
11n Ushijima S, Togo H. Synlett 2010; 1562
11o Ohmura R, Takahata M, Togo H. Tetrahedron Lett. 2010; 51: 4378
11p Ushijima S, Togo H. Synlett 2010; 1067
11q Ushijima S, Moriyama K, Togo H. Tetrahedron 2011; 67: 958
11r Ushijima S, Dohi S, Moriyama K, Togo H. Tetrahedron 2012; 68: 1436
11s Baba H, Moriyama K, Togo H. Synlett 2012; 1175
11t Ushijima S, Moriyama K, Togo H. Tetrahedron 2012; 68: 4701
11u Ushijima S, Moriyama K, Togo H. Tetrahedron 2012; 68: 4588
11v Dohi S, Moriyama K, Togo H. Tetrahedron 2012; 68: 6557

12 Zagulyaeva AA, Yusubov MS, Zhdankin VV. J. Org. Chem. 2010; 75: 2119
13 Mahajan US, Akamanchi KG. Synlett 2008; 987
14 Khanna MS, Grag CP, Kapoor RP. Tetrahedron Lett. 1992; 33: 1495
15 Su F, Zhang JZ, Jin GY, Qiu T, Zhao DJ, Jia HB. J. Chem. Res. 2009; 741
16 Cho BT, Yang WK, Choi OK. J. Chem. Soc., Perkin Trans. 1 2001; 1204
17 Hodson D, Holt G, Wall DK. J. Chem. Soc. C 1970; 971
18 Moroda A, Togo H. Tetrahedron 2006; 62: 12408
19 Kanna MS, Grag CP, Kapoor RP. Synlett 1992; 393
20 Floyd MB, Du MT, Fabio PF, Jacob LA, Johnson BD. J. Org. Chem. 1985; 50: 5022
21 Lee DM, Kwak SH, Lee KI. Bull. Korean Chem. Soc. 2009; 30: 1317