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 2016; 48(17): 2845-2850
DOI: 10.1055/s-0035-1561635
DOI: 10.1055/s-0035-1561635
paper
An Efficient Aziridination of Styrenes Promoted by Visible Light
Further Information
Publication History
Received: 17 March 2016
Accepted after revision: 06 April 2016
Publication Date:
19 May 2016 (online)

Abstract
Styrenes reacted with sulfonamide in the presence of potassium carbonate and iodine in CHCl3 under visible light irradiation to produce the corresponding aziridines in moderate to good yields. A reaction mechanism to explain the formation of aziridines is also proposed.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1561635.
- Supporting Information
-
References
- 1a Ismail FM. D, Levitsky DO, Dembitsky VM. Eur. J. Med. Chem. 2009; 44: 3373
- 1b Majundar KC, Chattopadhyay SK. Heterocycles in Natural Product Synthesis . Wiley-VCH; Weinheim: 2011. Chap. 1
- 1c Thibodeaux CJ, Chang W-C, Liu H-W. Chem. Rev. 2012; 112: 1681
- 1d Bass PD, Guble DA, Judd TC, Williams RM. Chem. Rev. 2013; 113: 6816
- 1e Vandekerckhove S, D’hooghe M. Bioorg. Med. Chem. 2013; 21: 3643
- 2a Yudin AK. Aziridines and Epoxides in Organic Synthesis. Wiley-VCH; Weinheim: 2006
- 2b Comprehensive Heterocyclic Chemistry III . Vol. I. Katrizky AR, Ramsden CA, Scriven EF. V, Taylor RJ. K. Elsevier; Amsterdam: 2008
- 2c Sweeney JB. Chem. Soc. Rev. 2002; 31: 247
- 2d Lu P. Tetrahedron 2010; 66: 2549
- 2e Stanković S, D’hooghe M, Catak S, Eum H, Waroquier M, Speybroeck VV, De Kimpe N, Ha H-J. Chem. Soc. Rev. 2012; 41: 643
- 2f Cardoso AL, Pinho e Melo TM. V. D. Eur. J. Org. Chem. 2012; 6479
- 2g Hao YM, Paek S-M. Molecules 2013; 18: 9650
- 2h Ha H-J, Jung J-H, Lee WK. Asian J. Org. Chem. 2014; 3: 1020
- 2i Lim DS. W, Anderson EA. Synthesis 2012; 44: 983
- 3a Tanner D. Angew. Chem., Int. Ed. Engl. 1994; 33: 599
- 3b McCoull W, Davis FA. Synthesis 2000; 1347
- 3c Singh GS, D’hooghe M, De Kimpe N. Chem. Rev. 2007; 107: 2080
- 3d Degennaro L, Trinchera P, Luisi R. Chem. Rev. 2014; 114: 7881
- 3e Pellissier H. Adv. Synth. Catal. 2014; 356: 1899
- 3f Ohno H. Chem. Rev. 2014; 114: 7784
- 3g Zhu Y, Wang Q, Cornwall RG, Shi Y. Chem. Rev. 2014; 114: 8199
- 3h Callebaut G, Meiresonne T, De Kimpe N, Mangelinckx S. Chem. Rev. 2014; 114: 7954
- 4a Wenker H. J. Am. Chem. Soc. 1935; 57: 2328
- 4b Olofsson B, Wijtmans R, Somfai P. Tetrahedron 2002; 58: 5979
- 4c Buckley BR, Patel AP, Wijayantha KG. U. J. Org. Chem. 2013; 78: 1289
- 6a Li A.-H, Dai L-X, Aggarwal VK. Chem. Rev. 1997; 97: 2341
- 6b Aggarwal VK, Thompson A, Jones RV, Standen MC. H. J. Org. Chem. 1996; 61: 8368
- 6c Saito T, Sakairi M, Akiba D. Tetrahedron Lett. 2001; 42: 5451
- 6d Kokotos CG, Aggarwal VK. Org. Lett. 2007; 9: 2099
- 6e Rejeev R, Sunoj RB. Org. Biomol. Chem. 2011; 9: 2123
- 6f Huang M-T, Wu H-Y, Chein R-J. Chem. Commun. 2014; 50: 1101
- 6g Illa O, Namutebi M, Saha C, Ostovar M, Chen CC, Haddow MF, Thibault SN, Lusi M, McGarrigle EM, Aggarwal VK. J. Am. Chem. Soc. 2013; 135: 11951
- 7a Sweeney J. Eur. J. Org. Chem. 2009; 4911
- 7b Devis FA, Liu H, Zhou P, Fang T, Reddy GV, Zhang Y. J. Org. Chem. 1999; 64: 7559
- 7c Troisi L, Granito C, Carlucci C, Bona F, Florio S. Eur. J. Org. Chem. 2006; 775
- 7d Larson SE, Li G, Rowland GB, Junge D, Huang R, Woodcock HL, Antilla JC. Org. Lett. 2011; 13: 2188
- 7e Boultwood T, Affron DP, Trowbridge AD, Bull JA. J. Org. Chem. 2013; 78: 6632
- 8a Müller P, Fruit C. Chem. Rev. 2003; 103: 2905
- 8b Hashimoto T, Gálvez AO, Maruoka K. J. Am. Chem. Soc. 2013; 135: 17667
- 8c Künzi SA, Morandi B, Carreira EM. Org. Lett. 2012; 14: 1900
- 8d Guan Y, López-Alberca MP, Lu Z, Zhang Y, Desai AA, Patwardhan AP, Dai Y, Vetticatt MJ, Wulff WD. Chem. Eur. J. 2014; 20: 13894
- 9a Minakata S, Komatsu M. J. Synth. Org. Chem. Jpn. 2003; 61: 706
- 9b Rubin AE, Sharpless KB. Angew. Chem., Int. Ed. Engl. 1997; 36: 2637
- 9c Ando T, Kano D, Minakata S, Ryu I, Komatsu M. Tetrahedron 1998; 54: 13485
- 9d Jain SL, Sharma VB, Sain B. Tetrahedron Lett. 2004; 45: 8731
- 9e Karabal PU, Chouthaiwale PV, Shaikh TM, Suryavanshi G, Sudalai A. Tetrahedron Lett. 2010; 51: 6460
- 10a Chang JW. W, Ton TM. U, Chan PW. H. Chem. Rec. 2011; 11: 331
- 10b Evans DA, Faul MM, Bilodeau MT. J. Am. Soc. Chem. 1994; 116: 2742
- 10c Gillespie KM, Sanders CJ, O’Shaughnessy P, Westmoreland I, Thickitt CP, Scott P. J. Org. Chem. 2002; 67: 3450
- 10d Zdilla MJ, Abu-Omar M. J. Am. Chem. Soc. 2006; 126: 16971
- 10e Kiyokawa K, Kosaka T, Minakata S. Org. Lett. 2013; 15: 4858
- 11a Uchida T, Katsuki T. Chem. Rec. 2014; 14: 117
- 11b Omura K, Uchida T, Irie R, Komatsu T. Chem. Commun. 2004; 2060
- 11c Abu-Omar MM, Shields CE, Edwards NY, Eikey RA. Angew. Chem. Int. Ed. 2005; 44: 6203
- 11d Cramer SA, Jenkins DM. J. Am. Chem. Soc. 2011; 133: 19342
- 11e Zardi P, Pozzoli A, Ferretti F, Manca G, Meaklli C, Gallo E. Dalton Trans. 2015; 44: 10479
- 11f Scholz SO, Farney EP, Kim S, Bates DM, Yoon TP. Angew. Chem. Int. Ed. 2016; 55: 2239
- 12a Dauban P, Sanière L, Tarrade A, Dodd RH. J. Am. Chem. Soc. 2001; 123: 7707
- 12b Liang J.-L, Yuan S.-X, Huang J.-S, Che C.-M. J. Org. Chem. 2004; 69: 3610
- 12c Li Z, Ding X, He C. J. Org. Chem. 2006; 71: 5876
- 12d Yoshimura A, Nemykin VN, Zhdankin VV. Chem. Eur. J. 2011; 17: 10538
- 13a Anderson DJ, Glichrist TL, Horwell DC, Rees CW. J. Chem. Soc. C 1970; 576
- 13b Atkinson RS, Malpass JR. J. Chem. Soc., Perkin Trans. 1 1977; 2242
- 13c Li J, Liang J.-L, Chan PW. H, Che C.-M. Tetrahedron Lett. 2004; 45: 2685
- 13d Richardson RD, Desaize M, Wirth T. Chem. Eur. J. 2007; 13: 6745
- 13e Yoshimura A, Middleton KR, Zhu C, Nemykin VN, Zhdankin VV. Angew. Chem. Int. Ed. 2012; 51: 8059
- 13f Chen J, Yan W.-Q, Lam CM, Zeng C.-C, Hu L.-M, Little RD. Org. Lett. 2015; 17: 986
- 14 Kariya A, Yamaguchi T, Nobuta T, Tada N, Miura Y, Itoh A. RSC Adv. 2014; 4: 13191
- 15 For cleavage of N–I bond by visible light, see: O’Broin CQ, Fernández P, Martínez C, Muñiz K. Org. Lett. 2016; 18: 436
- 16 Nagasawa Y, Tanba K, Tada N, Yamaguchi E, Itoh A. Synlett 2015; 26: 412
- 17 Nobuta T, Hirashima S, Tada N, Miura T, Itoh A. Synlett 2010; 2335
- 18 Guang-Yao G, Harden JD, Zhang XP. Org. Lett. 2005; 7: 3191
- 19 Chung-Yang H, Doyle AG. J. Am. Chem. Soc. 2012; 134: 9541
- 20 Evans DA, Faul MM, Bilodeau MT. J. Am. Chem. Soc. 1994; 116: 2742
For some examples of imino Corey–Chaykovski reaction, see:
For some examples of aza-Darzens reaction, see:
For some examples of carbene insertion, see:
For some examples using chloramine-T as nitrogen source, see:
For some examples using PhI=NTs as nitrogen source, see:
For some examples using azide as nitrogen source, see:
For some examples using sulfonamide as nitrogen source, see:
For metal-free aziridination, see:
For some examples using phthalimide as nitrogen source, see:
For metal-free aziridinaion, see: