Development of cellulose-supported Pd-nanocatalyst for the heck coupling and michael addition reactions

• Agricultural waste corncob cellulose supported palladium nanocomplexes (PdNc-PHA) were synthesized and thoroughly characterized. • The PdNc-PHA demonstrated excellent catalytic performance (0.03 mol%) in Mizoroki-Heck reactions of inactivated aryl/hetero aryl chlorides with a wide range of olefins. • The PdNc-PHA was also smoothly forwarded (0.03 mol%) aza-Micheal addition reactions of phenol/thiophenols and cyclic/alicyclic amines with ofefins to give O, S and N -alkylated products with excellent yield. • The nanocomplex was recovered and reused ten times without noticeably losing any of its activity in the Heck reaction. The development of reusable, bio-resource based nanocatalysts with high turnover numbers (TONs) is essential for increased sustainability in the chemical sector. Herein, cellulose-supported bio-resourced poly(hydroxamic acid) is employed as a ligand in the synthesis of a palladium nanocomposite ( PdNc-PHA ) that exhibits higher TONs that previously reported similar systems for the Mizoroki-Heck and Michael addition reactions. The PdNc-PHA catalyst was characterised using Fourier transform infrared spectroscopy (FTIR), field-emission scanning electron microscopy (FE-SEM), energy dispersive X-ray spectrometry (EDX), high-resolution transmission electron microscopy (HR-TEM), X-ray photoelectron spectroscopy (XPS), and inductively coupled plasma-atomic emission spectroscopy (ICP-AES) analyses. Results showed that the PdNc-PHA catalyst exhibits excellent durability and high catalytic activity in the Mizoroki-Heck and Michael addition reactions, leading to high yields of the desired corresponding products. The Mizoroki-Heck reaction of aryl/heteroaryl chlorides with olefins resulted in the production of cross-coupled products, while the Michael addition reaction of phenol/thiophenol and aliphatic cyclic/alicyclic amines with a variety of olefins synthesised the corresponding O-, S-, and N -alkylated products. The recycle and reusability of the catalyst were tested using 4-nitrochlorobenzene and butyl acrylate. The results demonstrated that the catalyst maintained its catalytic activity effectively for up to ten cycles without any noticeable loss in performance. This research represents a promising strategy for efficient catalysis based on bio-waste as a wealth material.

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Publication Details

Journal
Carbohydrate Polymer Technologies and Applications
Published
2024-10-09
DOI
https://doi.org/10.1016/j.carpta.2024.100578
Citations
3
Primary Topic
Catalytic Cross-Coupling Reactions
Type
article
Field-Weighted Citation Impact
0.75

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article

Development of cellulose-supported Pd-nanocatalyst for the heck coupling and michael addition reactions

Shaheen M. Sarkar, Mohd Hasbi Ab. Rahim, Md. Maksudur Rahman Khan, Kamrul Hasan et al.
3 citations
Carbohydrate Polymer Technologies and Applications
Catalytic Cross-Coupling Reactions
0.75
article

Development of cellulose-supported Pd-nanocatalyst for the heck coupling and michael addition reactions

Shaheen M. Sarkar, Mohd Hasbi Ab. Rahim, Md. Maksudur Rahman Khan, Kamrul Hasan, Emmet O’Reilly, Lutfor Rahman
article en
3 citations

Abstract

• Agricultural waste corncob cellulose supported palladium nanocomplexes (PdNc-PHA) were synthesized and thoroughly characterized. • The PdNc-PHA demonstrated excellent catalytic performance (0.03 mol%) in Mizoroki-Heck reactions of inactivated aryl/hetero aryl chlorides with a wide range of olefins. • The PdNc-PHA was also smoothly forwarded (0.03 mol%) aza-Micheal addition reactions of phenol/thiophenols and cyclic/alicyclic amines with ofefins to give O, S and N -alkylated products with excellent yield. • The nanocomplex was recovered and reused ten times without noticeably losing any of its activity in the Heck reaction. The development of reusable, bio-resource based nanocatalysts with high turnover numbers (TONs) is essential for increased sustainability in the chemical sector. Herein, cellulose-supported bio-resourced poly(hydroxamic acid) is employed as a ligand in the synthesis of a palladium nanocomposite ( PdNc-PHA ) that exhibits higher TONs that previously reported similar systems for the Mizoroki-Heck and Michael addition reactions. The PdNc-PHA catalyst was characterised using Fourier transform infrared spectroscopy (FTIR), field-emission scanning electron microscopy (FE-SEM), energy dispersive X-ray spectrometry (EDX), high-resolution transmission electron microscopy (HR-TEM), X-ray photoelectron spectroscopy (XPS), and inductively coupled plasma-atomic emission spectroscopy (ICP-AES) analyses. Results showed that the PdNc-PHA catalyst exhibits excellent durability and high catalytic activity in the Mizoroki-Heck and Michael addition reactions, leading to high yields of the desired corresponding products. The Mizoroki-Heck reaction of aryl/heteroaryl chlorides with olefins resulted in the production of cross-coupled products, while the Michael addition reaction of phenol/thiophenol and aliphatic cyclic/alicyclic amines with a variety of olefins synthesised the corresponding O-, S-, and N -alkylated products. The recycle and reusability of the catalyst were tested using 4-nitrochlorobenzene and butyl acrylate. The results demonstrated that the catalyst maintained its catalytic activity effectively for up to ten cycles without any noticeable loss in performance. This research represents a promising strategy for efficient catalysis based on bio-waste as a wealth material.

Carbohydrate Polymer Technologies and ApplicationsVol. 8
Universiti Malaysia Pahang Al-Sultan Abdullah (MY), Universiti of Malaysia Sabah (MY), Universiti Teknologi Brunei (BN), University of Limerick (IE), University of Sharjah (AE), Shannon Applied Biotechnology Centre (IE)
Science Foundation Ireland, Universiti Malaysia Sabah
Openalex Percentile: Top 32%
Catalytic Cross-Coupling Reactions
0.75
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