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Hydroxyapatite supported palladium catalysts for Suzuki-Miyaura cross-coupling reaction in aqueous medium

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Title Hydroxyapatite supported palladium catalysts for Suzuki-Miyaura cross-coupling reaction in aqueous medium
 
Creator INDRA, A
GOPINATH, CS
BHADURI, S
LAHIRI, GK
 
Subject LINKED AMPHIPHILIC POLYMER
N-HETEROCYCLIC CARBENE
ARYL CHLORIDES
HIGHLY EFFICIENT
LIGAND-FREE
HETEROGENEOUS CATALYST
HETEROARYL HALIDES
ASSEMBLED COMPLEX
FACILE SYNTHESIS
WATER
 
Description Supported palladium catalyst 1 has been prepared by the immobilisation of [Pd(COD)Cl-2] (COD = 1,5-cyclooctadiene) on hydroxyapatite. Catalyst 2 has been prepared by subsequent reduction of catalyst 1 with sodium borohydride in ethanol. Under similar reaction conditions, catalyst 1 with Pd2+, is found to be almost five times more active than 2. Using 1 as the catalyst and water as the solvent, reaction conditions for Suzuki-Miyaura cross-coupling reactions have been optimised under aerobic conditions. The best catalytic activities are observed in the presence of potassium carbonate as the base and tetrabutylammonium bromide as a promoter. Catalyst 1 has been tested for catalytic cross-coupling reactions with sixteen different, electronically neutral, electron rich, electron poor and sterically hindered aryl boronic acids, and several different aryl halides including aryl chlorides. More than thousand turnovers and high selectivities to the hetero-coupled products have been observed in most cases. For many substrates the turnovers with 1 are notably more than what has been reported with other supported catalysts in water. The recyclability and scale-up potential of catalyst 1 have been tested and found to be satisfactory. A negligible drop in activity is observed over ten recycles with an accumulated turnover number of similar to 30000.
 
Publisher ROYAL SOC CHEMISTRY
 
Date 2014-10-16T12:55:09Z
2014-10-16T12:55:09Z
2013
 
Type Article
 
Identifier CATALYSIS SCIENCE & TECHNOLOGY, 3(6)1625-1633
http://dx.doi.org/10.1039/c3cy00160a
http://dspace.library.iitb.ac.in/jspui/handle/100/15600
 
Language en