Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2017; 49(04): 917-924
DOI: 10.1055/s-0036-1588315
DOI: 10.1055/s-0036-1588315
paper
Green Organocatalytic Oxidation of Sulfides to Sulfoxides and Sulfones
Further Information
Publication History
Received: 29 June 2016
Accepted after revision: 26 August 2016
Publication Date:
21 September 2016 (online)
Abstract
A highly efficient synthetic methodology towards the selective synthesis of sulfoxides and sulfones is reported using a cheap and green organocatalytic method. Starting from sulfides and using 2,2,2-trifluoroacetophenone as the organocatalyst and H2O2 as the oxidant, the high-yielding preparation of sulfoxides or sulfones is described, being dependent on the reaction conditions.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588315.
- Supporting Information
-
References
- 1a Hartz RA, Arvanitis AG, Arnold C, Rescinito JP, Hung KL, Zhang G, Wong H, Langley DR, Gilligan PJ, Trainor GL. Bioorg. Med. Chem. Lett. 2006; 16: 934
- 1b Otzen T, Wempe EG, Kunz B, Bartels R, Lehwark-Yvetot G, Hänsel W, Schaper K.-J, Seydel JK. J. Med. Chem. 2003; 47: 240
- 1c Pal M, Rao Veeramaneni V, Nagabelli M, Rao Kalleda S, Misra P, Rao Casturi S, Rao Yeleswarapu K. Bioorg. Med. Chem. Lett. 2003; 13: 1639
- 1d Doherty GA, Kamenecka T, McCauley E, Van Riper G, Mumford RA, Tong S, Hagmann WK. Bioorg. Med. Chem. Lett. 2002; 12: 729
- 3 Yazdanyar S, Boer J, Ingvarsson G, Szepietowski JC, Jemec GB. E. Dermatology 2011; 222: 342
- 4 Sturino CF, O’Neill G, Lachance N, Boyd M, Berthelette C, Labelle M, Li L, Roy B, Scheigetz J, Tsou N, Aubin Y, Bateman KP, Chauret N, Day SH, Lévesque J.-F, Seto C, Silva JH, Trimble LA, Carriere M.-C, Denis D, Greig G, Kargman S, Lamontagne S, Mathieu M.-C, Sawyer N, Slipetz D, Abraham WM, Jones T, McAuliffe M, Piechuta H, Nicoll-Griffith DA, Wang Z, Zamboni R, Young RN, Metters KM. J. Med. Chem. 2007; 50: 794
- 5 Prasit P, Wang Z, Brideau C, Chan C.-C, Charleson S, Cromlish W, Ethier D, Evans JF, Ford Hutchinson AW, Gauthier JY, Gordon R, Guay J, Gresser M, Kargman S, Kennedy B, Leblanc Y, Leger S, Mancini J, O’Neill GP, Ouellet M, Percival MD, Perrier H, Riendeau D, Rodger I, Tagari P, Thérien M, Vickers P, Wong E, Xu L.-J, Young RN, Zamboni R, Boyce S, Rupniak N, Forrest M, Visco D, Patrick D. Bioorg. Med. Chem. Lett. 1999; 9: 1773
- 6a Carreno MC. Chem. Rev. 1995; 95: 1717
- 6b Fernandez I, Khiar N. Chem. Rev. 2003; 103: 3651
- 6c Caron S, Dugger RW, Ruggeri SG, Ragan JA, Ripin DH. B. Chem. Rev. 2006; 106: 2943
- 6d Metzner P, Thuillier A. Sulfur Reagents in Organic Synthesis . Academic Press; London: 1994
- 6e Synthesis of Sulfones, Sulfoxides and Cyclic Sulfides . Patai S, Rappoport Z. John Wiley; Chichester: 1994
- 6f Bentley R. Chem. Rev. 2005; 105: 609
- 7a Du L, Cao P, Xing J, Lou Y, Jiang L, Li L, Liao J. Angew. Chem. Int. Ed. 2013; 52: 4207
- 7b Qi W.-Y, Zhu T.-S, Xu M.-H. Org. Lett. 2011; 13: 3410
- 7c Jin S.-S, Wang H, Xu M.-H. Chem. Commun. 2011; 47: 7230
- 7d Chen J, Chen J.-M, Lang F, Zhang X.-Y, Cun L.-F, Zhu J, Deng J.-G, Liao J. J. Am. Chem. Soc. 2010; 132: 4552
- 7e Chen Q.-A, Dong X, Chen M.-W, Wang D.-S, Zhou Y.-G, Li Y.-X. Org. Lett. 2010; 12: 1928
- 7f Lang F, Li D, Chen J.-M, Chen J, Li L.-C, Cun L.-F, Zhu J, Deng J.-G, Liao J. Adv. Synth. Catal. 2010; 352: 843
- 8a Suwanborirux K, Charupant K, Amnuoypol S, Pummangura S, Kubo A, Saito N. J. Nat. Prod. 2002; 65: 935
- 8b Kim S, Kubec R, Musah RA. J. Ethnopharmacol. 2006; 104: 188
- 8c Dini I, Tenore GC, Dini A. J. Nat. Prod. 2008; 71: 2036
- 8d El-Aasr M, Fujiwara Y, Takeya T, Tsukamoto S, Ono M, Nakamo D, Okawa M, Kinjo J, Yoshimitsu H, Nohara T. J. Nat. Prod. 2010; 73: 1306
- 9a Li H, He L, Lu J, Zhu W, Jiang X, Wang Y, Tan Y. Energy Fuels 2009; 23: 1354
- 9b Zhu W, Li H, Jiang X, Yan Y, Lu J, He J, Xia J. Green Chem. 2008; 10: 641
- 9c He L, Li H, Zhu W, Guo J, Jiang X, Lu J, Yan Y. Ind. Eng. Chem. Res. 2008; 47: 6890
- 9d Li H, Jiang X, Zhu W, Lu J, Shu H, Yan Y. Ind. Eng. Chem. Res. 2009; 48: 9034
- 9e Huang W, Zhu W, Li H, Shi H, Zhu G, Li H, Chen G. Ind. Eng. Chem. Res. 2010; 49: 8998
- 9f Ding Y, Zhu W, Li H, Jeng W, Zhang M, Duan Y, Chang Y. Green Chem. 2011; 13: 1210
- 9g Zhu W, Ding Y, Li H, Qin J, Yanhong Y, Xiong J, Xu Y, Liu H. RSC Adv. 2013; 3: 3893
- 9h Lissner E, de Souza WF, Ferrera B, Dupont J. ChemSusChem 2009; 2: 962
- 10a Jana NK, Verkade JG. Org. Lett. 2003; 5: 3787
- 10b Griffin RJ, Henderson A, Curtin NJ, Echalier A, Endicott JA, Hardcastle IR, Newell DR, Noble NE. M, Wang LZ, Golding BT. J. Am. Chem. Soc. 2006; 128: 6012
- 10c Pace V, Castoldi L, Holzer W. Tetrahedron Lett. 2012; 53: 967
- 11 Varma RS, Naicker KP. Org. Lett. 1999; 1: 189
- 12 Fukuda N, Ikemoto T. J. Org. Chem. 2010; 75: 4629
- 13 Varma RS, Saini RK, Meshram HM. Tetrahedron Lett. 1997; 38: 6525
- 14 Yu B, Liu AH, He LN, Li B, Diao ZF, Li YN. Green Chem. 2012; 34: 957
- 15 Hanson P, Hendrickx RA. A. J, Smith JR. L. New J. Chem. 2010; 34: 65
- 16a Legros J, Bolm C. Angew. Chem. Int. Ed. 2003; 42: 5487
- 16b Legros J, Bolm C. Angew. Chem. Int. Ed. 2004; 43: 4225
- 16c Bagherzadeh M, Amini N. Inorg. Chem. Commun. 2009; 21
- 16d Egami H, Katsuki T. J. Am. Chem. Soc. 2007; 129: 8940
- 16e Li B, Liu A.-H, He L.-N, Yang Z.-Z, Gao J, Chen K.-H. Green Chem. 2012; 14: 130
- 17a Bagherzadeh M, Latifi R, Tahsini L, Amini M. Catal. Commun. 2008; 10: 196
- 17b Bagherzadeh M, Tahsini L, Latifi R. Catal. Commun. 2008; 9: 1600
- 17c Xie F, Fu Z, Zhong HS, Ye ZP, Zhou XP, Liu FL, Rong CY, Mao LQ, Yin DL. J. Mol. Catal. A: Chem. 2009; 307: 93
- 18 Wu X.-F. Tetrahedron Lett. 2012; 53: 4328
- 19 Van de Velde F, Arends IW. C. E, Sheldon RA. J. Inorg. Biochem. 2000; 80: 81
- 20 Lindén AA, Johansson M, Hermanns N, Bäckvall J.-E. J. Org. Chem. 2006; 71: 3849
- 21 Jereb M. Green Chem. 2012; 14: 3047
- 22a Karimi B, Khorasani M. ACS Catal. 2013; 3: 1657
- 22b Shi X.-Y, Wei J.-F. J. Mol. Catal. A: Chem. 2008; 280: 142
- 22c Shi X, Han X, Ma W, Wei J, Li J, Zhang Q, Chen Z. J. Mol. Catal. A: Chem. 2008; 341: 57
- 22d Das SP, Boruah JJ, Sharma N, Islam NS. J. Mol. Catal. A: Chem. 2012; 356: 36
- 22e Karimi B, Ghoreishi-Nezhad M, Clark JH. Org. Lett. 2005; 7: 625
- 22f Rajabi F, Naserian S, Primo A, Luque R. Adv. Synth. Catal. 2011; 353: 2060
- 22g Boruah JJ, Das SP, Ankireddy SR, Gogoi SR, Islam NS. Green Chem. 2013; 15: 2944
- 22h Doherty S, Knight JG, Carroll MA, Ellison JR, Hobson SJ, Stevens S, Hardacre C, Goodrich P. Green Chem. 2015; 17: 1559
- 23a Limnios D, Kokotos CG. ACS Catal. 2013; 3: 2239
- 23b Limnios D, Kokotos CG. Chem. Eur. J. 2014; 20: 559
- 23c Limnios D, Kokotos CG. J. Org. Chem. 2014; 79: 4270
- 23d Theodorou A, Limnios D, Kokotos CG. Chem. Eur. J. 2015; 21: 5238
- 23e Voutyritsa E, Theodorou A, Kokotos CG. Org. Biomol. Chem. 2016; 16: 5708
- 24 Celebre G, De Luca G, Maiorino M, Iemma F, Ferrarini A, Pieraccini S, Spada GP. J. Am. Chem. Soc. 2005; 127: 11736
- 25 Zhang H, Liao J, Zhu J, Yu B, Deng J. Green Chem. 2009; 11: 1401
- 26 Kirihara M, Yamamoto J, Noguchi T, Itou A, Naito S, Hirai Y. Tetrahedron 2009; 65: 10477
- 27 Jia T, Bellomo A, Montel S, Zhang M, EL Baina K, Zheng B, Walsh PJ. Angew. Chem. Int. Ed. 2014; 53: 260
- 28 Shukla VG, Salgaonkar PD, Akamanchi KG. J. Org. Chem. 2003; 68: 5422
- 29 Yamaguchi T, Matsumoto K, Saito B, Katsuki T. Angew. Chem. Int. Ed. 2007; 46: 4729
- 30 Clennan EL, Zhou W, Chan J. J. Org. Chem. 2002; 67: 9368
- 31 Veerakumara P, Lub Z.-Z, Velayudhamb M, Lub K.-L, Rajagopal S. J. Mol. Catal. A: Chem. 2010; 332: 128
- 32 Della EW, Graney SD. J. Org. Chem. 2004; 69: 3824
- 33 Block E, De Orazio R, Thiruvazhi M. J. Org. Chem. 1994; 59: 2273
- 34 Denmark SE, Cresswell AJ. J. Org. Chem. 2013; 78: 12593
- 35 Margraf N, Manolikakes G. J. Org. Chem. 2015; 80: 2582
- 36 Venier CG, Squires TG, Chen Y.-Y, Hussmann GP, Shei JC, Smith BF. J. Org. Chem. 1982; 47: 3773
- 37 Karimi B, Khorasani M. ACS Catal. 2013; 3: 1657
- 38 Rafiee E, Rahpeyma N. Chin. J. Catal. 2015; 36: 1342