Abstract
The ionic liquid based methylchloroiminium chloride reagent (Vilsmeier reagent) derived from DMF-like multipurpose functional ionic liquid has been used as an efficient and reusable reagent for Mitsunobu reaction. Variety of different alcohols has been converted into different classes of compounds under ionic liquid conditions. The present system offers a competitive and better alternative to routine Mitsunobu protocol.
Highlights
The Mitsunobu reaction is a direct intermolecular or intramolecular substitution reaction of alcohols with weaker nucleophillic reagents mediated by diethyl azodicarboxylate (DEAD) and tri-coordinate phosphorus compounds, such as Ph3P, (Me2N)P etc
We investigated the scope of this protocol for various structural variants of nucleophiles with alcohols
After optimization of reaction conditions, we scrutinized the scope of present protocol from various aspects
Summary
The Mitsunobu reaction is a direct intermolecular or intramolecular substitution reaction of alcohols with weaker nucleophillic reagents mediated by diethyl azodicarboxylate (DEAD) and tri-coordinate phosphorus compounds, such as Ph3P, (Me2N)P etc. The Mitsunobu reaction has found wide spread use in many fields because of its high versatility and extensive applicability (Mitsunobu, 1981; Hughes, 1992, 1996). The Mitsunobu reaction has been widely used for the re-functionalization of alcohols, as well as for inversion of hydroxyl group. Considerable bulk of research has been done to expand the scope of Mitsunobu reaction and it has been used to achieve key organic transformations and major steps in different total synthesis schemes. 2009; Mitsunobu, 1981; Hughes, 1992)
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