Stable and Reusable Binaphthyl‐Supported Palladium Catalyst for Aminocarbonylation of Aryl Iodides

Sharma, Nidhi; Sekar, Govindasamy

doi:10.1002/adsc.201500642

Cited by 37 publications

(22 citation statements)

References 79 publications

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“…Notably, FT‐IR spectra of both 1 and 2 reveal the disappearance of ν (COO) asymmetric band of acetate group, previously observed at 1600 cm −1 for Pd(OAc) 2 , confirming complete displacement of OAc – after solid‐state annealing . In addition, the intensity of two bands at 621 and 1161 cm −1 , assignable to imidazolium units is sharply reduced or almost disappeared for both 1 and 2 , suggesting the formation of Pd(II)/Pd(0)‐NHC bond (Figure S3) . We further characterized 1 and 2 using 29 Si and 13 C CP/MAS spectroscopy (Figure S4 and S5).…”

Section: Methodsmentioning

confidence: 99%

Solid-state Synthesis of Polyhedral Oligomeric Silsesquioxane-Supported N-Heterocyclic Carbenes/Imidazolium salts on Palladium Nanoparticles: Highly Active and Recyclable Catalyst

et al. 2016

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We describe a novel and green synthetic methodology for the fabrication of polyhedral oligomeric silsesquioxane-supported N-heterocyclic carbenes/imidazolium salts on palladium(II) complexes; Pd(II)-MPIm-POSS (1) composite by solid-state annealing between Pd(OAc) 2 and octakis(3-(1-methylimidazolium)propyl) octasilsesquioxane without added base. Subsequently, arylboronic acid based in situ or ex situ reduction of 1 in aqueous ethanol produces polyhedral oligomeric silsesquioxane-supported N-heterocyclic carbenes/imidazolium salts on palladium nanoparticles; Pd(0)-nano-POSS (2) composite, consisting of monodispersed and N-heterocyclic carbene (NHC) stabilized Pd nanoparticles of very small size (3.0 AE 1.5 nm). Nanocatalyst 2 is a highly efficient and easily recyclable homogeneous catalyst for Suzuki-Miyaura cross-coupling reactions with TOF up to 1670 h À1 .Palladium nanoparticles stabilized on solid supports have been used in various applications including chemical sensor and catalysis, particularly for reduction and C-C coupling reactions. [1] Over the past decades, development of an efficient and environmentally friendly method to fabricate monodispersed metal nanoparticles with definite size and shape, high catalytic activity, exceptional stability, and multiple recyclability is highly desirable for practical applications. In particular, novel methods for the fabrication of palladium nanocomposites on a non-toxic support and stabilizer have been actively pursued. [2] In this context due to strong s donating properties and coordinating ability to the metal center, the N-heterocyclic carbene (NHC) has shown to be an excellent ligand for transition metals as well as metal nanoparticles. [3] Despite many examples of NHC ligands in homogeneous metal-catalyzed chemical transformations and polymer synthesis, fewer reports involving carbene stabilized d block metal nanoparticles are known with limited applications. [4]

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Section: Methodsmentioning

confidence: 99%

Solid-state Synthesis of Polyhedral Oligomeric Silsesquioxane-Supported N-Heterocyclic Carbenes/Imidazolium salts on Palladium Nanoparticles: Highly Active and Recyclable Catalyst

et al. 2016

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“…Sekar et al prepared PdNPs capped with 1,1′-binaphthyl-2,2′-bis(diazoniumtetrafluoroborate) ligand by reducing H 2 [PdCl 4 ] with sodium borohydride in toluene [ 149 ]. The as-prepared nanoparticles were characterized by TEM, showing well-dispersed small particles (3.3 ± 0.9 nm); this nano-catalyst exhibited high activity for the direct annulation of benzamides, aminocarbonylations and cross-coupling reactions [ 149 , 150 , 151 ]. PdNPs stabilized by binaphthyl ligand were applied as well for the synthesis of indanones through one-pot carbene migration/Heck type cyclization reaction ( Scheme 36 a) [ 152 ].…”

Section: Palladium Nanoparticlesmentioning

confidence: 99%

Palladium and Copper: Advantageous Nanocatalysts for Multi-Step Transformations

et al. 2021

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Metal nanoparticles have been deeply studied in the last few decades due to their attractive physical and chemical properties, finding a wide range of applications in several fields. Among them, well-defined nano-structures can combine the main advantages of heterogeneous and homogenous catalysts. Especially, catalyzed multi-step processes for the production of added-value chemicals represent straightforward synthetic methodologies, including tandem and sequential reactions that avoid the purification of intermediate compounds. In particular, palladium- and copper-based nanocatalysts are often applied, becoming a current strategy in the sustainable synthesis of fine chemicals. The rational tailoring of nanosized materials involving both those immobilized on solid supports and liquid phases and their applications in organic synthesis are herein reviewed.

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“…More recently, transition metal catalyzed oxidative amidation of alcohols or aldehydes with amines has been developed for amides synthesis (path b, c) . Alternative approaches including the carbonylation of alkyl or benzyl halides with amines (path d),, the reaction of substituted alkynyl bromides with amines (path e), the amidation of carboxylic acids with tert ‐amines through C−N bond cleavage (path f), and the oxidative coupling of carboxylic acids with formamides (path g) have been introduced. However, many of these approaches are problematic regarding cost and atom‐efficiency, as well as functional group tolerance and recyclability.…”

Section: Introductionmentioning

confidence: 99%

Air‐stable Bis(pentamethylcyclopentadienyl) Zirconium Perfluorooctanesulfonate as an Efficient and Recyclable Catalyst for the Synthesis of N‐substituted Amides

et al. 2018

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Bis(pentamethylcyclopentadienyl) zirconium perfluorooctanesulfonate is an air-stable and water-tolerant Lewis acid. This complex exhibited good thermal stability and high solubility in polar organic solvents. The compound showed relatively strong acidity, with an acid strength of 0.8 < Ho 3.3, and high catalytic efficiency for the synthesis of N-substituted amides via the reaction of carboxylic acids with amines, the Ritter reaction of nitriles with alcohols, and the amination of alcohols with amides. Moreover, the complex had good reusability. This catalytic system affords a simple and efficient way to synthesize N-substituted amides.

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Stable and Reusable Binaphthyl‐Supported Palladium Catalyst for Aminocarbonylation of Aryl Iodides

Cited by 37 publications

References 79 publications

Solid-state Synthesis of Polyhedral Oligomeric Silsesquioxane-Supported N-Heterocyclic Carbenes/Imidazolium salts on Palladium Nanoparticles: Highly Active and Recyclable Catalyst

Solid-state Synthesis of Polyhedral Oligomeric Silsesquioxane-Supported N-Heterocyclic Carbenes/Imidazolium salts on Palladium Nanoparticles: Highly Active and Recyclable Catalyst

Palladium and Copper: Advantageous Nanocatalysts for Multi-Step Transformations

Air‐stable Bis(pentamethylcyclopentadienyl) Zirconium Perfluorooctanesulfonate as an Efficient and Recyclable Catalyst for the Synthesis of N‐substituted Amides

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