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LiBF 4 integrated into [BMIm]BF 4 : an ionic‐liquid metal composite and homogeneous catalyst for efficient synthesis of pyran‐annulated heterocycles
Author(s) -
RadMoghadam Kurosh,
Taghizadeh Valadi Alireza,
Alipour Arefeh
Publication year - 2014
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.3099
Subject(s) - chemistry , ionic liquid , catalysis , solvent , metal , inorganic chemistry , ionic bonding , organic chemistry , ion
The ionic liquid [BMIm]BF 4 doped with LiBF 4 was found to efficiently catalyze the three‐component reaction between isocyanides, acetylenic esters and enols or phenols at room temperature, leading to rapid synthesis of 2‐aminopyran‐annulated systems in fairly high yields. Efficiency of this catalysis and its benefits in terms of improved yields and reaction times could be ascribed to involvement of relatively stable organolithium intermediates which make the reaction more feasible. The ionic solution tolerates a significant amount of dissolved LiBF 4 , while remaining fluid at room temperature to serve as solvent for the organic substrates. It retains its initial integrity after use and recovery, as it could be recycled several times without appreciable catalytic decrements. The catalytic activity of the ionic composite is completely lost in the absence of LiBF 4 . Copyright © 2014 John Wiley & Sons, Ltd.