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Synlett 2012; 23(18): 2692-2698
DOI: 10.1055/s-0032-1317473
DOI: 10.1055/s-0032-1317473
letter
A Facile and Green Protocol for Nucleophilic Substitution Reactions of Sulfonate Esters by Recyclable Ionic Liquids [bmim][X]
Further Information
Publication History
Received: 10 August 2012
Accepted: 17 September 2012
Publication Date:
23 October 2012 (online)
Abstract
Ionic liquids [bmim][X] (X = Cl, Br, I, OAc, SCN) are highly efficient reagents for nucleophilic substitution reactions of sulfonate esters derived from primary and secondary alcohols. The counter anions (X–) of the ionic liquids, [bmim][X], effectively replace the sufonates affording the corresponding substitution products such as alkyl halides, acetates, and thiocyanides in excellent yields. The newly developed protocol is very environmentally attractive because the reactions use stoichiometric amounts of ionic liquids as sole reagents in most cases and do not require additional solvents, any other activating reagents, non-conventional equipment, or special precautions. Moreover, these ionic liquids can be readily recycled without loss of reactivity, making the whole process ‘greener’.
Key words
ionic liquids - nucleophilic substitution - halogenation - recyclability - green chemistrySupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
- Supporting Information
-
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