Synthesis and Characterization of N,N-Dimethylformamide-Protected Palladium Nanoparticles and Their Use in the Suzuki–Miyaura Cross-Coupling Reaction

Abstract

Herein, the synthesis of new N,N-dimethylformamide (DMF)-protected palladium nanoparticles (Pd NPs-OAc) employing Pd (OAc)2 ( Pd­(OCOCH3)2) as the NP precursor is reported. Pd NPs-OAc were comprehensively characterized by transmission electron microscopy, FT-IR, NMR, and X-ray photoelectron spectroscopy to determine the Pd NP size distribution and the coordination state of DMF. Pd NPs-OAc were compared with Pd NPs-Cl, using PdCl2 as the NP precursor. The Suzuki–Miyaura cross-coupling reaction proceeded efficiently in the presence of Pd NPs-OAc and a high catalytic activity was observed with a turnover number of up to 1.5 × 105. Furthermore, the Pd NP-OAc catalysts could be recycled at least five times.

Synthesis of new Schiff bases; Investigation of their in situ catalytic activity for Suzuki CC coupling reactions and antioxidant activities

“…After filtering rapidly through SiO 2 , internal standard was added, and GC–MS was taken. The biphenyl product was characterized by 1 H NMR and GC, and agreement with the literature data 59–63 …”

“…The biphenyl product was characterized by 1 H NMR and GC, and agreement with the literature data. [59][60][61][62][63]…”

Shielding Effect of Nanomicelles: Stable and Catalytically Active Oxidizable Pd(0) Nanoparticle Catalyst Compatible for Cross-Couplings of Water-Sensitive Acid Chlorides in Water

“…Excellent functional group tolerance was also observed in this transformation. Functional groups such as formyl (35,42,43,45), chloro (34,40,47,48,50), cyano (33,38,39,42,44), fluoro (33,35,37,38,(42)(43)(44)47), nitro (34,41,49), ketone (37,48,49), trifluoromethyl (32), and amide (47) were all well-tolerated. Various heterocyclic boronic acids possessing benzodioxane (40,44), benzothiophene (38,39), and thiophene (32,46) residues showed good-to-excellent reactivity.…”

“…Hence, solvent-stabilized Pd(0) NPs have recently emerged as a viable alternative. 32 − 34 Traditionally, the synthesis of such NPs relies on toxic organic solvents, such as DMF 34 , 35 and NMP, 36 where the solvent’s tertiary amide group plays a vital role in stabilizing the NP.…”

“…Hence, solvent-stabilized Pd(0) NPs have recently emerged as a viable alternative. 32−34 Traditionally, the synthesis of such NPs relies on toxic organic solvents, such as DMF 34,35 and NMP, 36 where the solvent's tertiary amide group plays a vital role in stabilizing the NP. Designing an amphiphile possessing structural features similar to DMF and NMP could enable the synthesis, stabilization, and applications of phosphine-free Pd(0) NPs under aqueous conditions.…”