Efficient and Eco-Friendly Perspectives for C-H Arylation of Benzothiazole Utilizing Pd Nanoparticle-Decorated Chitosan
Open Access
Abstract
In this contribution, an eco-friendly, sustainable, and efficient palladium nanoparticle-decorated chitosan (Pd@Chitosan) catalyst was synthesized by a simple impregnation method. The synthesized material was utilized as a heterogeneous catalyst for the C-H arylation of benzothiazole under ultrasonic irradiation. The Pd@Chitosan catalyst efficiently catalyzed the conversion of aryl iodides and bromides to 1-(4-(benzothiazol-2-yl)phenyl)ethan-1-one selectively. A single product of 83–93% yield was obtained in N,N-dimethylformamide solvent at 80 °C for 2.5h. This study reveals that Pd@Chitosan is an efficient catalyst, which catalyzes the C-H arylation with good reaction yields. The activity of the Pd@Chitosan is due to the presence of highly dispersed Pd(0) nanoparticles on the surface of the chitosan and Pd2+; a tentative mechanism was proposed based on the XPS results of the fresh catalyst and spent catalyst.Keywords
Funding Information
- Deanship of Scientific Research (DSR) at King Abdulaziz University (G:163-130-1440)
This publication has 57 references indexed in Scilit:
- Chitosan biopolymer for fuel cell applicationsCarbohydrate Polymers, 2013
- Pd(II)-catalyzed ortho arylation of 2-arylbenzothiazoles with aryl iodides via benzothiazole-directed C–H activationJournal of Organometallic Chemistry, 2012
- Chitosan functionalized ionic liquid as a recyclable biopolymer-supported catalyst for cycloaddition of CO2Green Chemistry, 2012
- Bimetallic Palladium Catalysis: Direct Observation of Pd(III)−Pd(III) IntermediatesJournal of the American Chemical Society, 2009
- Palladium(II)‐Catalyzed C-H Activation/C-C Cross‐Coupling Reactions: Versatility and PracticalityAngewandte Chemie International Edition, 2009
- Direct Functionalization of Nitrogen Heterocycles via Rh-Catalyzed C−H Bond ActivationAccounts of Chemical Research, 2008
- State of palladium in palladium-aluminosilicate catalysts as studied by XPS and the catalytic activity of the catalysts in the deep oxidation of methaneKinetics and Catalysis, 2007
- Chemical modification of chitosan by phosphorylation: an XPS, FT-IR and SEM studyJournal of Biomaterials Science, Polymer Edition, 2005
- A review of chitin and chitosan applicationsReactive and Functional Polymers, 2000
- Effect of gamma-irradiation on surface and catalytic properties of CuO−ZnO/Al2O3 systemJournal of Radioanalytical and Nuclear Chemistry, 1997