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 2015; 47(22): 3542-3552
DOI: 10.1055/s-0034-1378821
DOI: 10.1055/s-0034-1378821
paper
Mild and Efficient Reductive Deoxygenation of Epoxides to Olefins with Tin(II) Chloride/Sodium Iodide as a Novel Reagent
Further Information
Publication History
Received: 12 May 2015
Accepted after revision: 19 June 2015
Publication Date:
10 August 2015 (online)
Abstract
A highly efficient and green protocol is reported for the reductive deoxygenation of organic epoxides to olefins using tin(II) chloride/sodium iodide as a novel reagent. The reaction gives an excellent yield (85–96%) in ethanol under reflux within 2–10 minutes, without affecting other functional groups. The advantages of our method are the use of inexpensive reagents, the eco-friendly and green reaction conditions, and the short reaction times and high yields.
Key words
deoxygenation - aliphatic and aromatic epoxides - alkenes - tin(II) chloride/sodium iodideSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1378821.
- Supporting Information
-
References
- 1a Madesclaire M. Tetrahedron 1988; 44: 6537
- 1b Abad A, Concepción P, Corma A, García H. Angew. Chem. Int. Ed. 2005; 44: 4066
- 1c Hayashi T, Tanaka K, Haruta M. J. Catal. 1998; 178: 566
- 1d Bailie JE, Hutchings GJ. Chem. Commun. 1999; 2151
- 1e Zhang X, Shi H, Xu BQ. Angew. Chem. Int. Ed. 2005; 44: 7132
-
1f Girard P, Namy JL, Kagan HB. J. Am. Chem. Soc. 1980; 102: 2693
- 1g Concellon JM, Bardales E. Org. Lett. 2002; 4: 189
- 1h Martin MG, Ganem B. Tetrahedron Lett. 1984; 25: 251
- 1i Davis RE. J. Org. Chem. 1958; 23: 1767
- 1j Neureiter NP, Bordwell FG. J. Am. Chem. Soc. 1959; 81: 578
- 1k Snyder HR, Stewart JM, Ziegler JB. J. Am. Chem. Soc. 1947; 69: 2672
- 1l Aalbersberg WG. L, Vollhardt KP. C. J. Am. Chem. Soc. 1977; 99: 2792
- 1m Iranpoor N, Kazemi F. Synthesis 1996; 821
- 1n Shoppee CW, Sternhell S, Taylor WC. Aust. J. Chem. 1966; 19: 1265
- 1o Mahesh M, Murphy JA, Wassel HP. J. Org. Chem. 2005; 70: 4118
- 1p Firouzabadi H, Iranpoor N, Jafarpour M. Tetrahedron Lett. 2004; 45: 7454
- 2a Silverman RB. J. Am. Chem. Soc. 1981; 103: 3910
- 2b Preusch PC, Suttie JW. J. Org. Chem. 1983; 48: 3301
- 3a Gable KP, Brown EC. Synlett 2003; 2243
- 3b Isobe H, Branchaud BP. Tetrahedron Lett. 1999; 40: 8747
- 3c Itoh T, Nagano T, Sato M, Hirobe M. Tetrahedron Lett. 1989; 30: 6387
- 4 Marples BA, Muxworthy JP, Baggaley KH. Synlett 1992; 646
- 5 Csuk R, Dorr P. Tetrahedron 1994; 50: 9983
- 6 Yamada N, Mizuochi M, Morita H. Tetrahedron 2007; 63: 3408
- 7 Kai K, Takeuchi J, Kataoka T, Yokoyama M, Watanabe N. Tetrahedron 2008; 64: 6760
- 8 Comprehensive Organic Name Reactions and Reagents. Wang Z. John Wiley & Sons; Singapore: 2010: 2659
- 9 Kundu A, Prabhakar S, Vairamani M, Roy S. Organometallics 1997; 16: 4796
- 10 Isobe H, Branchaud BP. Tetrahedron Lett. 1999; 40: 8747
- 11 Clive DL. J, Menchen SM. J. Org. Chem. 1980; 45: 2347
- 12 Righi G, Bovicelli P, Sperandio A. Tetrahedron 2000; 56: 1733
- 13 Gable KP, Brown EC. Organometallics 2000; 19: 944
- 14 Moloy KG. Inorg. Chem. 1988; 27: 677
- 15a Ahmed N, Pathe GK, Venkata BB. Tetrahedron Lett. 2014; 55: 3683
- 15b Ahmed N, Van Lier JE. Tetrahedron Lett. 2007; 48: 5407
- 15c Ahmed N, Van Lier JE. Tetrahedron Lett. 2006; 47: 2725
- 15d Ahmed N, Konduru NK. Beilstein J. Org. Chem. 2012; 8: 177
- 15e Konduru NK, Ahmed N. Synth. Commun. 2013; 43: 2008
- 15f Ahmed N, Venkata BB, Kumar H. Synthesis 2011; 2471