Issue 6, 2013

Hydroxyapatite supported palladiumcatalysts for Suzuki–Miyaura cross-coupling reaction in aqueous medium

Abstract

Supported palladium catalyst 1 has been prepared by the immobilisation of [Pd(COD)Cl2] (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 ∼30 000.

Graphical abstract: Hydroxyapatite supported palladium catalysts for Suzuki–Miyaura cross-coupling reaction in aqueous medium

Supplementary files

Article information

Article type
Paper
Submitted
07 Mar 2013
Accepted
25 Mar 2013
First published
26 Mar 2013

Catal. Sci. Technol., 2013,3, 1625-1633

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

A. Indra, C. S. Gopinath, S. Bhaduri and G. Kumar Lahiri, Catal. Sci. Technol., 2013, 3, 1625 DOI: 10.1039/C3CY00160A

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements