Enol esters are the most vital moieties to construct different organic scaffolds thus play a significant role in a variety of synthetic transformations. Owing to their immense importance as substrates and intermediates in organic synthesis, polymer and pharmaceutical chemistry and as industrially important compounds, attempts have been made to synthesize substituted enol esters.[1] So far, a large number of methodologies has been developed for the synthesis of enol esters. Among them, the direct addition of carboxylic acids to alkynes is the most widely used atom economical approach.[2] However, it is very challenging to control the regio- and stereoselectivity during the addition process especially in the case of unsymmetrically substituted internal alkynes. Therefore, the main focus of the ongoing research has shifted towards efficient synthesis of widely substituted stereo-defined enol esters, by the use of specific reagents and catalysts. Various transition metal complexes of ruthenium, palladium, rhodium, iridium, cobalt and copper are being widely utilized for the hydrocarboxylation of the alkynes to synthesize substituted enol esters.[3] Most of these aforementioned approaches are assisted by either toxic or expensive metal catalysts, drastic reaction conditions, lengthy troublesome procedures, poisonous reagents and costly ligands, while reports on metal free hydrocarboxylation reactions are rather limited. We have disclosed the first example of transition metal-free [BMIM]OH mediated hydrocarboxylation of alkynylnitriles, leading to a library of nitrile substituted enol esters. The operational simplicity, high efficiency, use of easily available inexpensive reagents, mild reaction conditions, high atom economic, general applicability, recyclability of the ionic liquid and complete regio- and stereoselectivity are the salient features of this method.

Transition Metal-free Ionic Liquid [BMIM]OH Mediated Regio- and Stereoselective Hydrocarboxylation of Alkynylnitriles

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27th CRSI National Symposium in Chemistry

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