Subscribe to RSS
DOI: 10.1055/s-0028-1087807
Martin Sulfurane - A Versatile Reagent for Organic Synthesis
Publication History
Publication Date:
24 February 2009 (online)
![](https://www.thieme-connect.de/media/synlett/200905/lookinside/thumbnails/10.1055-s-0028-1087807-1.jpg)
Introduction
Martin Sulfurane, a diphenylsulfur compound, has been a versatile reagent in organic synthesis since the 1970s.
Figure 1
The Sulfurane is reactive towards active hydrogen compounds and is one of the reagents of choice for a class of reactions including dehydration, amide cleavage, epoxide formation, sulfinimine synthesis, oxidation and coupling. [¹] The Martine Sulfurane has been prepared from hexafluoro-2-phenyl-2-propanol using KOH, diphenylsulfide and bromine. [¹] The general mechanism of action involves the rapid exchange of one of the alkoxy ligands on the sulfurane, followed by ionisation giving an alkoxysulfonium ion, which, in turn, undergoes E1 or E2 elimination. [²] Since Martin Sulfurane is a mild and neutral reagent, these reactions are quite compatible with a wide range of functional groups like carbamate, carbonyl, ester, ether, etc. The reagent is applicable to the synthesis of many natural products.
- 1
Martin JC.Arhart RJ.Franz JA.Perozzi EF.Kaplan LJ. Org. Synth. 1988, Coll. Vol. 6: 163 - 2
Martin JC.Arhart RJ. J. Am. Chem. Soc. 1972, 94: 5003 - 3
Sani M.Fossati G.Huguenot F.Zanda M. Angew. Chem. Int. Ed. 2007, 46: 3526 - 4
Nicolaou KC.Toh Q.Chen YK. J Am. Chem. Soc. 2008, 130: 11292 - 5
Wensley AM.Hardy AO.Gonsalves KM.Koviach JL. Tetrahedron Lett. 2007, 48: 2431 - 6
Yokokawa F.Shioiri T. Tetrahedron Lett. 2002, 43: 8679 - 7
Franz JA.Martin JC.Arhart RJ. J. Am. Chem. Soc. 1974, 96: 4604 - 8
Franz JA.Martin JC. J. Am. Chem. Soc. 1973, 95: 201 - 9
Franz JA.Martin JC. J. Am. Chem. Soc. 1975, 97: 583 - 10
Moslin RM.Jamison TF. J. Am. Chem. Soc. 2006, 128: 15106 - 11
Slaitas A.Yeheskiely E. J. Pep. Res. 2002, 60: 283