Journal
NEW JOURNAL OF CHEMISTRY
Volume 47, Issue 27, Pages 12861-12873Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d3nj00613a
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A reusable polymer-embedded Pd nanoparticle dip-catalyst membrane was developed to meet the criteria for a successful catalyst, including simple fabrication, high efficiency, stability, flexibility, straightforward recovery, reusability, and ease of scale-up. This membrane achieved high yields in various C-C bond formation reactions and moderate to good yields in C-X bond formations under mild reaction conditions. The system demonstrated stability, no significant leaching of Pd, and functional group tolerance.
The criteria for the development of a successful catalyst are simple yet cheap fabrication, high efficiency, stability, flexibility, straightforward recovery, reusability, and ease of scale-up. There are reports of palladium nanoparticle (PdNP)-based catalysts for performing carbon-carbon cross-coupling reactions, but the aforesaid criteria are rarely met in a single system. Moreover, a single catalyst system performing different types of C-C and C-heteroatom cross-coupling reactions is very rare. Herein, we achieved the above-mentioned criteria by using a reusable polymer-embedded Pd nanoparticle dip-catalyst membrane without any other ligands or additives under milder reaction conditions. The composite membrane was fabricated by simply depositing poly(4-vinyl pyridine) anchored PdNPs (average size 9.9 nm) onto a nylon-6 membrane followed by UV cross-linking. C-C bond formation reactions using diverse reagents (Suzuki-Miyaura, Heck, Sonogashira, Stille, Hiyama reactions) were achieved to give the desired products in high to excellent isolated yields, while C-X (X = N/O/S) bond formations were accomplished in moderate to good isolated yields. The turnover number (TON) and frequency (TOF) for the Suzuki-Miyaura cross-coupling reaction are calculated as & GE;x10(4) and 3.11 s(-1), respectively. The P4VP-PdNP dip-catalyst system was stable under the reaction conditions without significant leaching of Pd into the solution. The dip-catalyst membrane can be reused at least 10 times without losing any significant activity. The substrate scope for most of the cross-coupling reactions was tested, which indicates functional group tolerance and that the coupling reaction can take place with moieties having electron donating or withdrawing groups.
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