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.
Authors
- Shaheen M. Sarkar
- Mohd Hasbi Ab. Rahim (ORCID: https://orcid.org/0000-0002-1404-5838)
- Md. Maksudur Rahman Khan (ORCID: https://orcid.org/0000-0001-6594-5361)
- Kamrul Hasan (ORCID: https://orcid.org/0000-0002-5868-9803)
- Emmet O’Reilly (ORCID: https://orcid.org/0000-0002-5740-0780)
- Lutfor Rahman (ORCID: https://orcid.org/0000-0003-3766-4284)
Institutions
- 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)
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
Funders
- Science Foundation Ireland
- Universiti Malaysia Sabah