A PPh<sub>3</sub> modified-chitosan supported Pd nanocatalyst for heterogeneous Suzuki–Miyaura cross coupling reactions

We describe the synthesis of a triazolyl-pyridine-based aminophosphine, N-(diphenylphosphaneyl)-6-(1-phenyl)-1H- (1,2,3-triazol-4-yl)H)N hereafter], and its palladium and platinum complexes and their catalytic application. The reaction of 1 with [M(COD)Cl 2 ] (M = Pd or Pt) afforded the cationic complex [(MCl){PN(H)N}-κ 3 -P,N,N]Cl [M = Pd (2) or Pt (3)]. Alternatively, compounds 2 and 3 were also synthesized by treating [2,6-{H 2 N(C 5 H 3 N)(C 2 HN 3 C 6 H 5 )}] (A) with [M(COD)Cl 2 ] (M = Pd or Pt), followed by the addition of stoichiometric amounts of PPh 2 Cl and Et 3 N. The neutral, dearomatized complexes [(MCl){PNN}-κ 3 -P,N,N] [M = Pd (4) or Pt (5)] were prepared by the deprotonation of the NH of 2 and 3 with 1 equiv of t BuOK. Compounds 4 and 5 were also synthesized stepwise by treating [2,6-{H 2 N(C 5 H 3 N)(C 2 HN 3 C 6 H 5 )}] (A) with [M-(COD)Cl 2 ] (M = Pd or Pt) to give intermediate complexes [{MCl 2 }2,6-{NH 2 (C 5 H 3 N)(C 2 HN 3 C 6 H 5 )-κ 2 -N,N}] [M = Pd (B) or Pt (C)], which were subsequently phosphinated. The in situ-generated PNN ligand-stabilized Pd nanoparticles from compound 2 catalyzed the annulation of o-bromobenzaldehyde with alkynes to yield indenone derivatives. Mechanistic investigations suggested that the reaction was catalyzed by Pd nanoparticles (Pd@2) generated from compound 2 and proceeded through sequential oxidative addition, alkyne insertion, and reductive elimination steps to produce indanone products.

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Cationic and Neutral Pd^II and Pt^II Pincer Complexes of Phosphinamino-Triazolyl-Pyridine [PN(H)N]: Pincer Ligand-Stabilized Palladium Nanoparticles and Their Catalytic Annulation of Internal Alkynes to Indenones

Sheokand

Balakrishna

2023

Inorg. Chem.

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In Situ Decorated Palladium Nanoparticles on Chitosan Beads as a Catalyst for Coupling Reactions

et al. 2023

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A green protocol for the in situ synthesis of Pd nanoparticles on chitosan beads (Pd NPs-CS) is reported without the need to use any toxic reducing agents. The preparation of the Pd nanoparticles catalyst was performed using a simple coordination reaction between the prepared chitosan beads and palladium ions (Pd NPs-CS). The obtained catalyst was characterized by different techniques, including SEM, EDX, DRX, and FTIR analyses. The Pd NPs-CS catalyst was investigated in the Suzuki–Miyaura cross-coupling reaction and Heck reaction under greener conditions, and the results show high catalytic activity and selectivity. The bead form of the Pd NPs-CS catalyst was easily separated from the reaction mixture to obtain the desired products, as confirmed by spectroscopic methods. This sustainable catalyst has the advantages of having sustainable organic reactions such as biopolymer support and recovery without significant loss of catalytic activity or selectivity.

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A PPh₃ modified-chitosan supported Pd nanocatalyst for heterogeneous Suzuki–Miyaura cross coupling reactions

Abstract: A PPh3 modified-chitosan support was synthesized by the acid-mediated addition reaction of the tris(4-vinylphenyl)phosphane ligand (3vPPh3) and chitosan (CS). The material was loaded with Pd(OAc)2 to furnish a supported Pd...

Cited by 2 publications

References 48 publications

Cationic and Neutral Pd^II and Pt^II Pincer Complexes of Phosphinamino-Triazolyl-Pyridine [PN(H)N]: Pincer Ligand-Stabilized Palladium Nanoparticles and Their Catalytic Annulation of Internal Alkynes to Indenones

Cationic and Neutral Pd^II and Pt^II Pincer Complexes of Phosphinamino-Triazolyl-Pyridine [PN(H)N]: Pincer Ligand-Stabilized Palladium Nanoparticles and Their Catalytic Annulation of Internal Alkynes to Indenones

In Situ Decorated Palladium Nanoparticles on Chitosan Beads as a Catalyst for Coupling Reactions

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A PPh3 modified-chitosan supported Pd nanocatalyst for heterogeneous Suzuki–Miyaura cross coupling reactions

Abstract: A PPh3 modified-chitosan support was synthesized by the acid-mediated addition reaction of the tris(4-vinylphenyl)phosphane ligand (3vPPh3) and chitosan (CS). The material was loaded with Pd(OAc)2 to furnish a supported Pd...

Cited by 2 publications

References 48 publications

Cationic and Neutral PdII and PtII Pincer Complexes of Phosphinamino-Triazolyl-Pyridine [PN(H)N]: Pincer Ligand-Stabilized Palladium Nanoparticles and Their Catalytic Annulation of Internal Alkynes to Indenones

Cationic and Neutral PdII and PtII Pincer Complexes of Phosphinamino-Triazolyl-Pyridine [PN(H)N]: Pincer Ligand-Stabilized Palladium Nanoparticles and Their Catalytic Annulation of Internal Alkynes to Indenones

In Situ Decorated Palladium Nanoparticles on Chitosan Beads as a Catalyst for Coupling Reactions

Contact Info

Product

Resources

About

A PPh₃ modified-chitosan supported Pd nanocatalyst for heterogeneous Suzuki–Miyaura cross coupling reactions

Cationic and Neutral Pd^II and Pt^II Pincer Complexes of Phosphinamino-Triazolyl-Pyridine [PN(H)N]: Pincer Ligand-Stabilized Palladium Nanoparticles and Their Catalytic Annulation of Internal Alkynes to Indenones

Cationic and Neutral Pd^II and Pt^II Pincer Complexes of Phosphinamino-Triazolyl-Pyridine [PN(H)N]: Pincer Ligand-Stabilized Palladium Nanoparticles and Their Catalytic Annulation of Internal Alkynes to Indenones