RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2017; 49(05): 1109-1121
DOI: 10.1055/s-0036-1588900
DOI: 10.1055/s-0036-1588900
paper
o-Iodoxybenzoic Acid (IBX)–Iodine Mediated One-Pot Deacylative Sulfonylation of 1,3-Dicarbonyl Compounds: A Synthesis of β-Carbonyl Sulfones
Weitere Informationen
Publikationsverlauf
Received: 22. Juli 2016
Accepted after revision: 28. September 2016
Publikationsdatum:
26. Oktober 2016 (online)
![](https://www.thieme-connect.de/media/synthesis/201705/lookinside/thumbnails/ss-2016-n0517-op_10-1055_s-0036-1588900-1.jpg)
Abstract
A combination of o-iodoxybenzoic acid (IBX) and a catalytic amount of iodine is found to promote a facile one-pot deacylative sulfonylation reaction of 1,3-dicarbonyl compounds with sodium sulfinates to yield β-carbonyl sulfones. The present method provides the target products bearing a wide variety of functional groups in one step and in good yields.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588900.
- Supporting Information
-
References
- 1a Meadows DC, Gervay-Hague J. Med. Res. Rev. 2006; 26: 793
- 1b Nielsen M, Jacobsen CB, Holub N, Paixão MW, Jørgensen KA. Angew. Chem. Int. Ed. 2010; 49: 2668
- 1c Alba A.-NR, Companyó X, Rios R. Chem. Soc. Rev. 2010; 39: 2018
- 1d Huang Y, Huo LJ, Zhang SQ, Guo X, Han CC, Li YF, Hou JH. Chem. Commun. 2011; 47: 8904
- 2a Wolf WM. J. Mol. Struct. 1999; 474: 113
- 2b Xiang J, Ipek M, Suri V, Massefski W, Pan N, Ge Y, Tam M, Xing Y, Tobin JF, Xu X, Tam S. Bioorg. Med. Chem. Lett. 2005; 15: 2865
- 2c Xiang J, Ipek M, Suri V, Tam M, Xing Y, Huang N, Zhang Y, Tobin J, Mansour TS, McKew J. Bioorg. Med. Chem. 2007; 15: 4396
- 2d Curti C, Laget M, Carle AO, Gellis A, Vanelle P. Eur. J. Med. Chem. 2007; 42: 880
- 3 Ihara M, Suzuki S, Taniguchi T, Tokunaga Y, Fukumoto K. Tetrahedron 1995; 51: 9873
- 4a Bartlett PA, Green III FR, Rose EH. J. Am. Chem. Soc. 1978; 100: 4852
- 4b Mandai T, Yanagi T, Araki K, Morisaki Y, Kawada M, Otera J. J. Am. Chem. Soc. 1984; 106: 3670
- 5 Baldwin JE, Adlington RM, Crouch NP, Hill RL, Laffey TG. Tetrahedron Lett. 1995; 36: 7925
- 6 Kumar A, Sharma S, Tripathi VD, Srivastava S. Tetrahedron 2010; 66: 9445
- 7 Sengupta S, Sarma DS, Mondal S. Tetrahedron: Asymmetry 1998; 9: 2311
- 8 Looker JJ. J. Org. Chem. 1966; 31: 2714
- 9 Kiren S, Padwa A. J. Org. Chem. 2009; 74: 7781
- 10 Curti C, Crozet MD, Vanelle P. Tetrahedron 2009; 65: 200
- 11 Huang X, Xue J. J. Org. Chem. 2007; 72: 3965
- 12 Swenson RE, Sowin TJ, Zhang HQ. J. Org. Chem. 2002; 67: 9182
- 13a Corey EJ, Chaykovsky M. J. Am. Chem. Soc. 1964; 86: 1639
- 13b Trost BM, Arndt HC, Strege PE, Verhoeven TR. Tetrahedron Lett. 1976; 17: 3477
- 13c Kurth MJ, O’Brien MJ. J. Org. Chem. 1985; 50: 3846
- 13d Fujii M, Nakamura K, Mekata H, Oka S, Ohno A. Bull. Chem. Soc. Jpn. 1988; 61: 495
- 13e Guo H, Ye S, Wang J, Zhang Y. J. Chem. Res., Synop. 1997; 114
- 13f Sengupta S, Sarma DS, Mondal S. Tetrahedron 1998; 54: 9791
- 13g Guo H, Zhang Y. Synth. Commun. 2000; 30: 2559
- 14a Trost BM, Curran DP. Tetrahedron Lett. 1981; 22: 1287
- 14b Fan A.-L, Cao S, Zhang Z. J. Heterocycl. Chem. 1997; 34: 1657
- 14c Zweifel T, Nielsen M, Overgaard J, Jacobsen CB, Jørgensen KA. Eur. J. Org. Chem. 2011; 47
- 15a Vennstra GE, Zwaneburg B. Synthesis 1975; 519
- 15b Wildeman J, van Leusen AM. Synthesis 1979; 733
- 15c Xie Y.-Y, Chen Z.-C. Synth. Commun. 2001; 31: 3145
- 15d Suryakiran N, Reddy TS, Ashalatha K, Lakshman M, Venkateswarlu Y. Tetrahedron Lett. 2006; 47: 3853
- 15e Kumar D, Sundaree S, Rao VS, Varma RS. Tetrahedron Lett. 2006; 47: 4197
- 15f Suryakiran N, Prabhakar P, Rajesh K, Suresh V, Venkateswarlu Y. J. Mol. Catal. A: Chem. 2007; 270: 201
- 15g Sunitha P, Kumar KS, Rama Rao B, Venkateshwarlu G. Green Chem. Lett. Rev. 2008; 1: 179
- 15h Kumar A, Muthyala MK. Tetrahedron Lett. 2011; 52: 5368
- 15i Samakkanad N, Katrun P, Techajaroonjit T, Hlekhlai S, Pohmakotr M, Reutrakul V, Jaipetch T, Soorukram D, Kuhakarn C. Synthesis 2012; 44: 1693
- 16a Truce WE, Knospe RH. J. Am. Chem. Soc. 1955; 77: 5063
- 16b Truce WE, Bannister WW, Knospe RH. J. Org. Chem. 1962; 27: 2821
- 16c House HO, Larson JK. J. Org. Chem. 1968; 33: 61
- 16d Thomsen MW, Handwerker BM, Katz SA, Belser RB. J. Org. Chem. 1988; 53: 906
- 16e Ibarra CA, Rodríguez RC, Monreal MC. F, Navarro FJ. G, Tesorero JM. J. Org. Chem. 1989; 54: 5620
- 16f Katritzky AR, Abdel-Fattah AA. A, Wang M. J. Org. Chem. 2003; 68: 1443
- 17a Kamigata N, Udodaira K, Shimizu T. J. Chem. Soc., Perkin Trans. 1 1997; 783
- 17b Rawat VS, Reddy PL. M, Sreedhar B. RSC Adv. 2014; 4: 5165
- 18a Sreedhar B, Rawat VS. Synlett 2012; 23: 413
- 18b Lu Q, Zhang J, Wei F, Qi Y, Wang H, Liu Z, Lei A. Angew. Chem. Int. Ed. 2013; 52: 7156
- 18c Wei W, Liu C, Yang D, Wen J, You J, Suo Y, Wang H. Chem. Commun. 2013; 49: 10239
- 18d Lu Q, Zhang J, Zhao G, Qi Y, Wang H, Lei A. J. Am. Chem. Soc. 2013; 135: 11481
- 18e Handa S, Fennewald JC, Lipshutz BH. Angew. Chem. Int. Ed. 2014; 53: 3432
- 18f Chawla R, Singh AK, Yadav LD. S. Eur. J. Org. Chem. 2014; 2032
- 18g Wei W, Wen J, Yang D, Wu M, You J, Wang H. Org. Biomol. Chem. 2014; 12: 7678
- 18h Singh AK, Chawla R, Keshari T, Yadav VK, Yadav LD. S. Org. Biomol. Chem. 2014; 12: 8550
- 18i Singh AK, Chawla R, Yadav LD. S. Tetrahedron Lett. 2014; 55: 2845
- 18j Singh AK, Chawla R, Yadav LD. S. Tetrahedron Lett. 2014; 55: 4742
- 18k Liu C, Ding L, Guo G, Liu W. Eur. J. Org. Chem. 2016; 910
- 19 Holmquist CR, Roskamp EJ. Tetrahedron Lett. 1992; 33: 1131
- 20 Lu Q, Zhang J, Peng P, Zhang G, Huang Z, Yi H, Miller JT, Lei A. Chem. Sci. 2015; 6: 4851
- 21 Tang X, Huang L, Xu Y, Yang J, Wu W, Jiang H. Angew. Chem. Int. Ed. 2014; 53: 4205
- 22a Tang Y, Zhang Y, Wang K, Li X, Xu X, Du X. Org. Biomol. Chem. 2015; 13: 7084
- 22b Lu Q, Chen J, Liu C, Huang Z, Peng P, Wang H, Lei A. RSC Adv. 2015; 5: 24494
- 22c Tang Y, Fan Y, Gao H, Li X, Xu X. Tetrahedron Lett. 2015; 56: 5616
- 22d Yadav VK, Srivastava VP, Yadav LD. S. Synlett 2016; 27: 427
- 22e Yadav VK, Srivastava VP, Yadav LD. S. Tetrahedron Lett. 2016; 57: 2236
- 23 Frydman N, Mazur Y. J. Am. Chem. Soc. 1970; 92: 3203
- 24 Qian H, Huang X. Synthesis 2006; 1934
- 25 Tsui GC, Glenadel Q, Lau C, Lautens M. Org. Lett. 2011; 13: 208
- 26a Gao W.-C, Zhao J.-J, Chang H.-H, Li X, Liu Q, Wei W.-L. RSC Adv. 2014; 4: 49329
- 26b Gao W.-C, Zhao J.-J, Hu F, Chang H.-H, Li X, Wei W.-L. RSC Adv. 2015; 5: 25222
- 26c Pan X.-J, Gao J, Yuan G.-Q. Tetrahedron 2015; 71: 5525
- 27a Katrun P, Chiampanichayakul S, Korworapan K, Pohmakotr M, Reutrakul V, Jaipetch T, Kuhakarn C. Eur. J. Org. Chem. 2010; 5633
- 27b Sawangphon T, Katrun P, Chaisiwamongkhol K, Pohmakotr M, Reutrakul V, Jaipetch T, Soorukram D, Kuhakarn C. Synth. Commun. 2013; 43: 1692
- 27c Muangkaew C, Katrun P, Kanchanarugee P, Pohmakotr M, Reutrakul V, Soorukram D, Jaipetch T, Kuhakarn C. Tetrahedron 2013; 69: 8847
- 27d Katrun P, Muangkaew C, Pohmakotr M, Reutrakul V, Jaipetch T, Soorukram D, Kuhakarn C. J. Org. Chem. 2014; 79: 1778
- 27e Katrun P, Hongthong S, Hlekhlai S, Pohmakotr M, Reutrakul V, Soorukram D, Jaipetch T, Kuhakarn C. RSC Adv. 2014; 4: 18933
- 27f Katrun P, Hlekhlai S, Meesin J, Pohmakotr M, Reutrakul V, Jaipetch T, Soorukram D, Kuhakarn C. Org. Biomol. Chem. 2015; 13: 4785
- 27g Meesin J, Katrun P, Reutrakul V, Pohmakotr M, Soorukram D, Kuhakarn C. Tetrahedron 2016; 72: 1440
- 27h Meesin J, Katrun P, Pareseecharoen C, Pohmakotr M, Reutrakul V, Soorukram D, Kuhakarn C. J. Org. Chem. 2016; 81: 2744
- 28a Li X, Xu X, Shi X. Tetrahedron Lett. 2013; 54: 3017
- 28b Xiao F, Chen H, Xie H, Chen S, Yang L, Deng G.-J. Org. Lett. 2014; 16: 50
- 28c Kariya A, Yamaguchi T, Nobuta T, Tada N, Miura T, Itoh A. RSC Adv. 2014; 4: 13191
- 28d Singh R, Allam BK, Singh N, Kumari K, Singh SK, Singh KN. Org. Lett. 2015; 17: 2656
- 28e Wei W, Wen J, Yang D, Jing H, You J, Wang H. RSC Adv. 2015; 5: 4416
- 28f Zhang N, Yang D, Wei W, Yuan L, Cao Y, Wang H. RSC Adv. 2015; 5: 37013
- 28g Sun K, Lv Y, Zhu Z, Jiang Y, Qi J, Wu H, Zhang Z, Zhang G, Wang X. RSC Adv. 2015; 5: 50701
- 28h Gao J, Lai J, Yuan G. RSC Adv. 2015; 5: 66723
- 28i Chen J, Mao J, Zheng Y, Liu D, Rong G, Yan H, Zhang C, Shi D. Tetrahedron 2015; 71: 5059
- 28j Wang R, Zeng Z, Chen C, Yi N, Jiang J, Cao Z, Deng W, Xiang J. Org. Biomol. Chem. 2016; 14: 5317 ; and references cited therein
- 29a Swamer FW, Hauser CR. J. Am. Chem. Soc. 1950; 72: 1352
- 29b Allais C, Constantieux T, Rodriguez J. Chem. Eur. J. 2009; 15: 12945
- 29c He Z, Li H, Li Z. J. Org. Chem. 2010; 75: 4636
- 29d Liu X, Cheng R, Zhao F, Zhang-Negrerie D, Du Y, Zhao K. Org. Lett. 2012; 14: 5480
-
29e Ton TM. U, Tejo C, Tiong DL. Y, Chan PW. H. J. Am. Chem. Soc. 2012; 134: 7344
- 29f Dharma Rao GB, Acharya BN, Kaushik MP. Tetrahedron Lett. 2013; 54: 6644
- 29g Rudolph J, Aliagas I, Crawford JJ, Mathieu S, Lee W, Chao Q, Dong P, Rouge L, Wang W, Heise C, Murray LJ, La H, Liu Y, Manning G, Diederich F, Hoeflich KP. ACS Med. Chem. Lett. 2015; 6: 711
- 30a Cassani C, Bernardi L, Fini F, Ricci A. Angew. Chem. Int. Ed. 2009; 48: 5694
- 30b Kaupang Å, Bonge-Hansen T. Beilstein J. Org. Chem. 2013; 9: 1407
- 30c Stebbins JL, Zhang Z, Chen J, Wu B, Emdadi A, Williams ME, Cashman J, Pellecchia M. J. Med. Chem. 2007; 50: 6607
- 30d Stewart JD, Pinnick HW. Heterocycles 1987; 25: 213
- 30e Albrecht BK, Andersen DL, Bartberger M, Brown J, Brown R, Chaffee SC, Cheng Y, Croghan M, Graceffa R, Harried S, Hitchcock S, Hungate R, Judd T, Kaller M, Kreiman C, La D, Lopez P, Masse CE, Monenschein H, Nguyen T, Nixey T, Patel VF, Pennington L, Weiss M, Xue Q, Yang B, Zhong W. WO2007062007, 2007