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A novel imidazolium‐supported palladium–chloroglycine complex: copper‐ and solvent‐free high‐turnover catalysts for the Sonogashira coupling reaction
Author(s) -
Karthikeyan Parasuraman,
Muskawar Prashant Narayan,
Aswar Sachin Arunrao,
Bhagat Pundlik Rambhau,
Sythana Suresh Kumar
Publication year - 2012
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.2896
Subject(s) - chemistry , phenylacetylene , palladium , catalysis , sonogashira coupling , moiety , reagent , aryl , halide , medicinal chemistry , combinatorial chemistry , organic chemistry , polymer chemistry , alkyl
A novel, effective 1‐glycyl‐3‐methyl imidazolium chloride–palladium(II) complex ([Gmim]Cl–Pd(II)) was synthesized and studied as an organocatalyst for the Sonogashira coupling reaction under solvent‐free conditions at 25 °C. The hydrophobic group on amino acid favors reagent diffusion toward the chloroglycine moiety, increasing the catalytic activity of supported palladium complex. By this protocol, different aryl halides (Cl, Br and I) were reacted with phenylacetylene in good to excellent yields with turnover number 8.0 × 10 2 to 9.6 × 10 2 . The catalyst was recycled for the reaction of bromobenzene with phenylacetylene for eight runs without appreciable loss of its catalytic activity and negligible metal leaching. Copyright © 2012 John Wiley & Sons, Ltd.