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Synthesis 2019; 51(23): 4473-4486
DOI: 10.1055/s-0039-1690621
DOI: 10.1055/s-0039-1690621
paper
Hypervalent Iodine(III)-Catalyzed Epoxidation of β-Cyanostyrenes
Financial support by the DST New Delhi (Grant No.: SB/FT/CS-068/2014) is gratefully acknowledged.Further Information
Publication History
Received: 24 June 2019
Accepted after revision: 07 August 2019
Publication Date:
05 September 2019 (online)
Abstract
A convenient approach for the synthesis of β-cyanoepoxides is illustrated by iodine(III)-catalyzed epoxidation of electron-deficient β-cyanostyrenes, wherein the active catalytic iodine(III) species was generated in situ. The epoxidation of β-cyanostyrenes was performed using 10 mol% PhI as precatalyst in the presence of 2.0 equivalents Oxone as an oxidant and 2.4 equivalents of TFA as an additive at room temperature under ultrasonic radiations. The β-cyanoepoxides were isolated in good to excellent yields in a short reaction time.
Key words
epoxidation reaction - β-cyanostyrene - β-cyanoepoxide - iodobenzene - trifluoroacetic acid - OxoneSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1690621.
- Supporting Information
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References
- 1 Robert A, Baudy-Floc’h M, Le Grel P, Foucaud A. Trends Org. Chem. 1995; 5: 37; and references cited therein
- 2a Hamza-Reguig S, Bentabed-Ababsa G, Domingo LR, Rios-Gutierrez M, Philippot S, Fontanay S, Duval RE, Ruchaud S, Bach S, Roisnel T, Mongin F. J. Mol. Struct. 2018; 1157: 276
- 2b Serrar H, Boukhris S, Hassikou A, Souizi A. J. Heterocycl. Chem. 2015; 52: 1269
- 2c Pan J, Zhang W, Zhang J, Lu S. Tetrahedron Lett. 2007; 48: 2781
- 2d Grigoropoulou G, Clark JH, Elings JA. Green Chem. 2003; 5: 1
- 2e Seifi M, Sheibani H. ARKIVOC 2013; (iv): 191
- 3a Bentabed-Ababsa G, Hamza-Reguig S, Derdour A, Domingo LR, Saez JA, Roisnel T, Dorcet V, Nassare E, Mongin F. Org. Biomol. Chem. 2012; 10: 8434
- 3b Tagliapietra S, Cravotto G, Gaudino EC, Visentin S, Mussi V. Synlett 2012; 23: 1459
- 3c Domingo LR, Saez JA. J. Org. Chem. 2011; 76: 373
- 3d Volmajer J, Toplak R, Bittner S, Le Marechala AM. ARKIVOC 2003; (xiv): 49
- 3e Bentabed-Ababsa G, Derdour A, Roisnel T, Saez JA, Perez P, Chamorro E, Domingo LR, Mongin F. J. Org. Chem. 2009; 74: 2120
- 3f Bentabed G, Rahmouni M, Mongin F, Derdour A, Hamelin J, Bazureau JP. Synth. Commun. 2007; 37: 2935
- 4a Majcen-Le Marechal A, Le Grel P, Robert A, Biskup J, Ferk V, Toplak R. ARKIVOC 2001; 119
- 4b Roger F, Le Pironnec M.-G, Guerro M, Gougeon P, Gall P, Le Grel P, Baudy-Floc’h M. Synthesis 1999; 1341
- 4c Boukhris S, Souizi A. Tetrahedron Lett. 2000; 41: 2559
- 4d Amanetoullah AO, Chaabouni MM, Baklouti A.. Synth. Commun. 1996; 26: 1155
- 5a Guillemet M, Robert A, Baudy-Floc’h M.. Tetrahedron Lett. 1995; 36: 547
- 5b Majcen-Le Marechal A, Robert A, Leban I.. J. Chem. Soc., Perkin Trans. 1 1993; 351
- 5c Majcen-Le Marechal A, Robert A, Leban I. Tetrahedron 1990; 46: 451
- 5d Souizi A, Robert A. C. R. Acad. Sci. Paris, Ser. 2 1982; 295: 571
- 5e Robert A, Le Marechal A. J. Chem. Soc., Chem. Commun. 1978; 447
- 5f Ferrey M, Robert A, Foucaud A. C. R. Acad. Sci. Paris, Ser. C 1973; 277: 1153
- 6 Sekiya M, Suzuki K, Nanjo K. Chem. Pharm. Bull. 1981; 29: 336
- 7 Seeberger PH, Gilmore K, Ushakov DB. Chem. Commun. 2014; 50: 12649
- 8 Wang L, Wang Z, Li F, Zhang X, Yang F. Eur. J. Org. Chem. 2016; 1251
- 9 Lattanzi A, Vidal-Albalat A, Meninno S. Org. Lett. 2015; 17: 4348
- 10 Amrollahi MA, Mirhashemi F. Tetrahedron Lett. 2018; 59: 2661
- 11a Graham KM, Jasmin E. Tetrahedron Lett. 2018; 59: 2965
- 11b Chen Q, Gao G.-L. Curr. Organocatal. 2017; 4: 33
- 12a Akira N, Hodaka K, Junki T, Akira I, Tomohiro M, Yasuyoshi M. Org. Biomol. Chem. 2018; 16: 541
- 12b Kitamura T, Mizuno S, Muta K, Oyamada J. J. Org. Chem. 2018; 83: 2773
- 12c Fujita M. Tetrahedron Lett. 2017; 58: 4409
- 12d Mizar P, Wirth T. Angew. Chem. Int. Ed. 2014; 53: 5993
- 12e Singh FV, Wirth T. Synthesis 2013; 45: 2499; and references are cited therein
- 12f Kajiyama D, Saitoh T, Yamaguchi S, Nishiyama S. Synthesis 2012; 44: 1667
- 12g Wardrop DJ, Yermolina MV, Bowen EG. Synthesis 2012; 44: 1199
- 12h Singh FV, Wirth T. Org. Lett. 2011; 13: 6504
- 12i Du X, Chen H, Chen Y, Chen J, Liu Y. Synlett 2011; 1010
- 12j Wang H, Fan R. J. Org. Chem. 2010; 75: 6994
- 12k Moriarty RM, Tyagi S, Kinch M. Tetrahedron 2010; 66: 5801
- 12l Bose SS, Idrees M. Synthesis 2010; 393
- 12m Pardo LM, Tellitu I, Domínguez E. Synthesis 2010; 971
- 13a Jiang X, Zhu W, Yang L, Zheng Z, Yu C. Eur. J. Org. Chem. 2019; 2268
- 13b Shu S, Li Y, Jiang J, Ke Z, Liu Y. J. Org. Chem. 2019; 84: 458
- 13c Ghosh MK, Rajkiewicz AA, Kalek M. Synthesis 2019; 51: 359
- 13d Xing L, Zhang Y, Du Y.. Curr. Org. Chem. 2019; 23: 14
- 13e Dohi T, Sasa H, Dochi M, Yasui C, Kita Y. Synthesis 2019; 51: 1185
- 13f Jain N, Hein JE, Ciufolini MA. Synlett 2019; 30: 1222
- 13g Xing B, Ni C, Hu J. Angew. Chem. Int. Ed. 2018; 57: 9896
- 14 Singh FV, Mangaonkar SR, Kole PB. Synth. Commun. 2018; 48: 2169
- 15 Singh FV, Wirth T. Chem. Asian J. 2014; 9: 950; and references cited therein
- 16 Ushakov DB, Gilmore K, Seeberger PH. J. Org. Chem. 1997; 62: 7512
- 17 Denmark SE, Edwards MG. J. Org. Chem. 2006; 71: 7293
- 18 Singh FV, Rehbein J, Wirth T. ChemistryOpen 2012; 1: 245
- 19 Jimenez DE. Q, Ferreira IM, Birolli WG, Fonseca LP, Porto AL. M. Tetrahedron 2016; 72: 7317
- 20 Sen B, Akdere EH, Savk A, Gultekin E, Parali O, Goksu H, Sen F. Appl. Catal., B 2018; 225: 148
- 21 Ferreira JM. G. O, de Resende Filho JB. M, Batista PK, Teotonio EE. S, Vale JA. J. Braz. Chem. Soc. 2018; 29: 1382
- 22 Jiang W, Yang J, Liu Y.-Y, Song S.-Y, Ma J.-F. Inorg. Chem. 2017; 56: 3036
- 23 Lolak N, Kuyuldar E, Burhan H, Goksu H, Akocak S, Sen F. ACS Omega 2019; 4: 6848
- 24 Kharas GB, Russell SM, Cisler R, Capen TL, Chlupsa EA, Debellis LA, Duke JT. A, Frazier CB, Gora A, Kamenetsky E, Kurani AS, Kuta DL, Madison AL, Miramon PJ. J. Macromol. Sci., Part A: Pure Appl. Chem. 2008; 45: 261
- 25 Kharas GB, Russell SM, Ward DR, Doshi RM, Hijazin MY, Korkofigas E, Kuzenkova N, Leung B, Martinez H, Merchant FA, Meschbach NT, Opiola ES. J. Macromol. Sci., Part A: Pure Appl. Chem. 2008; 45: 133
- 26 Filho JB. M. R, Pires GP, Ferreira JM. G. O, Teotonio EE. S, Vale JA. Catal. Lett. 2017; 147: 167
- 27 Mitra AK, De A, Karchaudhuri N. Synth. Commun. 1999; 29: 2731
- 28 Meng D, Qiao Y, Wang X, Wen W, Zhao S. RSC Adv. 2018; 8: 30180
- 29 Wan J.-P, Jing Y, Liu Y, Sheng S. RSC Adv. 2014; 4: 63997
- 30 Panja SK, Dwivedi N, Saha S. RSC Adv. 2015; 5: 65626
- 31 Wang H, Li L, Bai X.-F, Deng WH, Zheng Z.-J, Yang K.-F, Xu L.-W. Green Chem. 2013; 15: 2349
- 32 Wiles C, Watts P, Haswell SJ, Pombo-Villar E. Tetrahedron 2005; 61: 10757
- 33 Yu Y.-Q, Wang Z.-L. J. Chin. Chem. Soc. 2013; 60: 288
- 34 Dev K, Maurya R. RSC Adv. 2015; 5: 13102
- 35 Zhang Y, Wen X, Shi Y, Yue R, Bai L, Liu Q, Ba X. Ind. Eng. Chem. Res. 2019; 58: 1142
- 36 Mayer RJ, Tokuyasu T, Mayer P, Gomar J, Sabelle S, Mennucci B, Mayr H, Ofial AR. Angew. Chem. Int. Ed. 2017; 56: 13279
- 37 Mennino S, Zullo L, Overgaard J, Lattanzi A. Adv. Synth. Catal. 2017; 359: 913
- 38 Miao C, Yan X, Xu D, Xia C, Sun W. Adv. Synth. Catal. 2017; 359: 476