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

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 (PdN...

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Main Authors: Shaheen M. Sarkar, Md Lutfor Rahman, Kamrul Hasan, Md. Maksudur Rahman Khan, Emmet J. O’Reilly, Mohd Hasbi Ab. Rahim
Format: Article
Language:English
English
Published: Elsevier Ltd. 2024
Subjects:
Q1-390 Science (General)
QD241-441 Organic chemistry
Online Access:https://eprints.ums.edu.my/id/eprint/41956/1/ABSTRACT.pdf
https://eprints.ums.edu.my/id/eprint/41956/2/FULL%20TEXT.pdf
https://eprints.ums.edu.my/id/eprint/41956/
https://doi.org/10.1016/j.carpta.2024.100578
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spelling my.ums.eprints.419562024-11-20T02:33:22Z https://eprints.ums.edu.my/id/eprint/41956/ Development of cellulose-supported Pd-nanocatalyst for the heck coupling and michael addition reactions Shaheen M. Sarkar Md Lutfor Rahman Kamrul Hasan Md. Maksudur Rahman Khan Emmet J. O’Reilly Mohd Hasbi Ab. Rahim Q1-390 Science (General) QD241-441 Organic chemistry 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 PdNcPHA 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 Nalkylated 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. Elsevier Ltd. 2024 Article NonPeerReviewed text en https://eprints.ums.edu.my/id/eprint/41956/1/ABSTRACT.pdf text en https://eprints.ums.edu.my/id/eprint/41956/2/FULL%20TEXT.pdf Shaheen M. Sarkar and Md Lutfor Rahman and Kamrul Hasan and Md. Maksudur Rahman Khan and Emmet J. O’Reilly and Mohd Hasbi Ab. Rahim (2024) Development of cellulose-supported Pd-nanocatalyst for the heck coupling and michael addition reactions. Carbohydrate Polymer Technologies and Applications, 8. pp. 1-12. ISSN 2666-8939 https://doi.org/10.1016/j.carpta.2024.100578
institution Universiti Malaysia Sabah
building UMS Library
collection Institutional Repository
continent Asia
country Malaysia
content_provider Universiti Malaysia Sabah
content_source UMS Institutional Repository
url_provider http://eprints.ums.edu.my/
language English
English
topic Q1-390 Science (General)
QD241-441 Organic chemistry
spellingShingle Q1-390 Science (General)
QD241-441 Organic chemistry
Shaheen M. Sarkar
Md Lutfor Rahman
Kamrul Hasan
Md. Maksudur Rahman Khan
Emmet J. O’Reilly
Mohd Hasbi Ab. Rahim
Development of cellulose-supported Pd-nanocatalyst for the heck coupling and michael addition reactions
description 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 PdNcPHA 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 Nalkylated 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.
format Article
author Shaheen M. Sarkar
Md Lutfor Rahman
Kamrul Hasan
Md. Maksudur Rahman Khan
Emmet J. O’Reilly
Mohd Hasbi Ab. Rahim
author_facet Shaheen M. Sarkar
Md Lutfor Rahman
Kamrul Hasan
Md. Maksudur Rahman Khan
Emmet J. O’Reilly
Mohd Hasbi Ab. Rahim
author_sort Shaheen M. Sarkar
title Development of cellulose-supported Pd-nanocatalyst for the heck coupling and michael addition reactions
title_short Development of cellulose-supported Pd-nanocatalyst for the heck coupling and michael addition reactions
title_full Development of cellulose-supported Pd-nanocatalyst for the heck coupling and michael addition reactions
title_fullStr Development of cellulose-supported Pd-nanocatalyst for the heck coupling and michael addition reactions
title_full_unstemmed Development of cellulose-supported Pd-nanocatalyst for the heck coupling and michael addition reactions
title_sort development of cellulose-supported pd-nanocatalyst for the heck coupling and michael addition reactions
publisher Elsevier Ltd.
publishDate 2024
url https://eprints.ums.edu.my/id/eprint/41956/1/ABSTRACT.pdf
https://eprints.ums.edu.my/id/eprint/41956/2/FULL%20TEXT.pdf
https://eprints.ums.edu.my/id/eprint/41956/
https://doi.org/10.1016/j.carpta.2024.100578
_version_ 1817843830797369344
score 13.223943

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