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
Download PDF
Synthesis 2016; 48(11): 1711-1718
DOI: 10.1055/s-0035-1561579
DOI: 10.1055/s-0035-1561579
paper
Alternative Protocol for the Synthesis of Symmetrical Dibenzyl Diselenides and Disulfides
Authors
Further Information
Publication History
Received: 12 December 2015
Accepted after revision: 15 February 2016
Publication Date:
22 March 2016 (online)
Abstract
A one-pot protocol for the preparation of symmetrical dibenzyl diselenides and disulfides from the corresponding benzyl alcohols employing NaBH2Se3 and NaBH2S3 as selenium-transfer and sulfur-transfer reagent, respectively, is described. Structurally diverse substituted benzyl alcohols afforded the corresponding diselenides and disulfides in good to excellent yields. The protocol is simple and mild, and the products were obtained within a short reaction time.
Key words
dibenzyl diselenides - dibenzyl disulfides - benzyl alcohols - selenating agent - NaBH2Se3 - NaBH2S3Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1561579.
- Supporting Information (PDF) (opens in new window)
-
References
- 1a Klayman DL, Guenter WH. H. Organoselenium Compounds: Their Chemistry and Biology . Wiley-Interscience; New York: 1973
- 1b Nicolaou KC, Petasis NA. Selenium in Natural Products Synthesis . CIS Inc; Philadelphia: 1984
- 1c Mugesh G, Du Mont WW, Sies H. Chem. Rev. 2001; 101: 2125
- 1d Nogueira CW, Zeni G, Rocha JB. T. Chem. Rev. 2004; 104: 6255
- 1e Stadtman TC. Science 1974; 183: 915
- 1f Illman D. Chem. Eng. News 1994; 72 (42): 53
- 1g Schwarz K, Fredga A. Bioinorg. Chem. 1974; 3: 153
- 2 Organoselenium Chemistry: Modern Developments in Organic Synthesis. In Topics in Current Chemistry. Vol. 208. Wirth T. Springer; Berlin: 2000
- 3a Fukuzawa S, Takahashi K, Kato H, Yamazaki H. J. Org. Chem. 1997; 62: 7711
- 3b Tomoda S, Iwaoka M. J. Chem. Soc., Chem. Commun. 1988; 1283
- 3c Tiecco M, Testaferri L, Santi C, Tomassini C, Marini F, Bagnoli L, Temperini A. Tetrahedron: Asymmetry 2000; 11: 4645
- 3d Tiecco M, Testaferri L, Marini F, Sternativo S, Santi C, Bagnoli L, Temperini A. Tetrahedron: Asymmetry 2001; 12: 3053
- 3e Back TG, Moussa Z, Parvez M. J. Org. Chem. 2002; 67: 499
- 3f Freudendahl DM, Shahzad SA, Wirth T. Eur. J. Org. Chem. 2009; 1649
- 3g Shahzad SA, Wirth T. Angew. Chem. Int. Ed. 2009; 48: 2588
- 4 Nishibayashi Y, Singh JD, Fukuzawa SI, Uemura S. J. Chem. Soc., Perkin Trans. 1 1995; 2871
- 5a Braga AL, Silva SJ. N, Ludtke DS, Drekener RL, Silveira CC, Rocha JB. T, Wessjohann LA. Tetrahedron Lett. 2002; 43: 7329
- 5b Santi C, Wirth T. Tetrahedron: Asymmetry 1999; 10: 1019
- 6a Wu X, Yu Z. Tetrahedron Lett. 2010; 51: 1500
- 6b Shahzad SA, Venin C, Wirth T. Eur. J. Org. Chem. 2010; 3465
- 6c Browne DM, Niyomura O, Wirth T. Org. Lett. 2007; 9: 3169
- 7a Iwaoka M, Katsuda T, Komatsu H, Tomoda S. J. Org. Chem. 2005; 70: 321
- 7b Schiesser CH, Sutej K. J. Chem. Soc., Chem. Commun. 1992; 57
- 8a Klayman DL, Griffin TS. J. Am. Chem. Soc. 1973; 95: 197
- 8b Gladysz J, Hornby JL, Garbe JE. J. Org. Chem. 1978; 43: 1204
- 8c Bergman J, Engman L. Synthesis 1980; 569
- 8d Syper L, Mlochowski J. Tetrahedron 1988; 44: 6119
- 8e Li JQ, Bao WL, Lue P, Zhou XJ. Synth. Commun. 1991; 21: 799
- 8f Wang J.-X, Cui W, Hu Y. J. Chem. Soc., Perkin Trans. 1 1994; 2341
- 8g Cordova-Reyes I, Vandenhoven E, Mohammed A, Pinto BM. Can. J. Chem. 1995; 73: 113
- 8h Hu X, Tian Z, Lu X, Chen Y. Synth. Commun. 1997; 27: 553
- 9a Salama P, Bernard C. Tetrahedron Lett. 1995; 36: 5711
- 9b Prabhu KR, Chandrasekaran S. Chem. Commun. 1997; 1021
- 9c Krief A, Delmotte C, Dumont W. Tetrahedron 1997; 53: 12147
- 9d Salama P, Bernard C. Tetrahedron Lett. 1998; 39: 745
- 9e Krief A, Dumont W, Delmotte C. Angew. Chem. Int. Ed. 2000; 39: 1669
- 9f Krief A. Tetrahedron Lett. 2002; 43: 3083
- 10a Krief A, De Mahieu AF, Dumont W, Trabelsi M. Synthesis 1988; 131
- 10b Krief A, Van Wemmel T, Redon M, Dumont W, Delmotte C. Angew. Chem. Int. Ed. 1999; 38: 2245
- 11 Singh D, Deobald AM, Camargo LR. S, Tabarelli G, Rodrigues OE. D, Braga AL. Org. Lett. 2010; 12: 3288
- 12 Tian F, Yu Z, Lu S. J. Org. Chem. 2004; 69: 4520
- 13 Wang JC, Cui W, Hu Y. J. Chem. Soc., Perkin Trans. 1 1994; 2341
- 14 Ming-De R, Hua-Rong Z, Wei-Qiang F, Xun-Jun Z. J. Organomet. Chem. 1995; 485: 19
- 15 Plano D, Baquedano Y, Moreno-Mateos D, Font M, Jiménez-Ruiz A, Palop JA, Sanmartín C. Eur. J. Med. Chem. 2011; 46: 3315
- 16 Soares LC, Alberto EE, Schwab RS, Taube PS, Nascimento V, Rodrigues OE. D, Braga AL. Org. Biomol. Chem. 2012; 10: 6595
- 17 Saravanan V, Porhiel E, Chandrasekaran S. Tetrahedron Lett. 2003; 44: 2257
- 18 Kimura Y, Matsuura D, Hanawa T, Kobayashi Y. Tetrahedron Lett. 2012; 53: 1116
- 19 Vishwanatha TM, Narendra N, Basab Chattopadhyay B, Mukherjee M, Sureshbabu VV. J. Org. Chem. 2012; 77: 2689
- 20 Lalancette JM, Arnac M. Can. J. Chem. 1969; 47: 3695
- 21 Lalancette JM, Freche A, Brindle R, Laliberte M. Synthesis 1972; 526
- 22a Bodzansky M. Principles of Peptide Synthesis . Springer-Verlag; Berlin: 1984. Chap. 4
- 22b Kishi Y, Nakatsuga S, Fukuyama T, Havel M. J. Am. Chem. Soc. 1973; 95: 6493
- 22c Tabashi K, Kawashima Y. Chem. Pharm. Bull. 1993; 41: 1066
- 22d Freeman F, Aregullin M, Rodriguez E. Rev. Heteroat. Chem. 1993; 9: 1
- 23a Atkinson JG, Hamel P, Girard Y. Synthesis 1988; 480
- 23b Shirani H, Janosik T. Synthesis 2007; 2690
- 24a Prabhu KR, Sivanand PS, Chandrasekaran S. Angew. Chem. Int. Ed. 2000; 39: 4316
- 24b Ranu BC, Mandal T. Synlett 2004; 1239
- 24c Bartolozzi A, Foudoulakis HM, Cole BM. Synthesis 2008; 2023
- 25 Movassagh B, Sobhani S, Kheirdoush F, Fadaei Z. Synth. Commun. 2003; 33: 3103
- 27 Fisher HL. Ind. Eng. Chem. 1950; 42: 1978
- 28a Iranpoor N, Zeynizadeh B. Synthesis 1999; 49
- 28b Iranpoor N, Firouzabadi H, Pourali AR. Tetrahedron 2002; 58: 5179
- 28c Ali MH, McDermott M. Tetrahedron Lett. 2002; 43: 6271
- 28d Kirihara M, Okubo K, Uchiyama T, Kato Y, Ochiai Y, Matsushita S, Hatano A, Kanamori K. Chem. Pharm. Bull. 2004; 52: 625
- 28e Akdag A, Webb T, Worley SD. Tetrahedron Lett. 2006; 47: 3509
- 28f Lenardao EJ, Lara RG, Silva MS, Raquel G, Jacob RG, Perin G. Tetrahedron Lett. 2007; 48: 7668
- 28g Kirihara M, Asai Y, Ogawa S, Noguchi T, Hatano A, Hirai Y. Synthesis 2007; 3286
- 28h Golchoubian H, Hosseinpoor F. Catal. Commun. 2007; 8: 697
- 28i Silveira CC, Mendes SR. Tetrahedron Lett. 2007; 48: 7469
- 28j Ozen R, Aydin F. Monatsh. Chem. 2006; 137: 307
- 29a Wang J.-X, Cui W, Hu Y. Synth. Commun. 1995; 25: 3573
- 29b Ilankumaran P, Prabhu KR, Chandrasekaran S. Synth. Commun. 1997; 27: 4031
- 29c Bandgar BP, Uppalla LS, Sadavarte VS. Tetrahedron Lett. 2001; 42: 6741
- 29d Wang J.-X, Gao L, Huang D. Synth. Commun. 2002; 32: 963
- 29e Polshettiwar V, Nivsarkar M, Acharya J, Kaushik MP. Tetrahedron Lett. 2003; 44: 887
- 29f Emerson DW, Bennett BL, Steinberg SM. Synth. Commun. 2005; 35: 631
- 29g Sonavane SU, Chidambaram M, Almog J, Sasson Y. Tetrahedron Lett. 2007; 48: 6048
- 29h Firouzabadi H, Iranpoor N, Abbasi M. Tetrahedron Lett. 2010; 51: 508
- 29i Soleiman-Beigi M, Mohammadi F. Tetrahedron Lett. 2012; 53: 7028
- 29j Kiasat AR, Mokhtari B, Kazemi F, Yousefi S, Javaherian M. J. Sulfur Chem. 2007; 28: 171
- 29k Kiasat AR, Mokhtari B, Savari A, Kazemi F. Phosphorus, Sulfur Silicon Relat. Elem. 2008; 183: 178
- 29l Firouzabadi H, Tamami B, Kiasat AR. Phosphorus, Sulfur Silicon Relat. Elem. 2000; 159: 99
- 29m Witt D. Synthesis 2008; 2491
- 30 Sinha S, Ilankumaran P, Chandrasekaran S. Tetrahedron 1999; 55: 14769
- 31 Gopinath P, Vidyarini R, Chandrasekaran S. Eur. J. Org. Chem. 2009; 6043
- 32 Lalancette JM, Freche A, Monteux R. Can. J. Chem. 1968; 46: 2754