On the Use of Diazonium Salts in the Design of Catalytic Hybrid Materials and Coatings

Mousli, Fatima; Snoussi, Youssef; Chehimi, Mohamed M.; Wojcieszak, Robert

doi:10.1007/978-3-031-04398-7_15

Cited by 3 publications

(4 citation statements)

References 77 publications

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“…These are bound to the surface by diazonium grafting using aryl amines with long alkyl tethers. , Conversion of the amine to a diazonium salt, followed by elimination of N 2 , generates a phenyl radical that binds to the surface, useful for the functionalization of carbon surfaces such as graphene, graphite, and carbon nanotubes. Such approaches are used to tune surface properties such as conductivity, thermoelectrics, and wettability . Grafting of this type was applied in sensing, catalysis, − and molecular electronics…”

Section: Introductionmentioning

confidence: 99%

“…Such approaches are used to tune surface properties such as conductivity, thermoelectrics, and wettability. 9 Grafting of this type was applied in sensing, 9 catalysis, 7−9 and molecular electronics. 10 Aryl amines can be synthesized by heterogeneous reduction of nitro aryls; 11−13 direct amination of halo aryls with ammonia using Cu, 14−17 Ni, 18 and Pd 19,20 catalytic systems; and selective direct catalyzed amination of CH bonds.…”

Section: ■ Introductionmentioning

confidence: 99%

“…Such approaches are used to tune surface properties such as conductivity, thermoelectrics, and wettability . Grafting of this type was applied in sensing, catalysis, − and molecular electronics…”

Section: Introductionmentioning

confidence: 99%

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Copper(I) Chloride Mediated Amination of Halobenzenes via Azides: Scope, Mechanistic Aspects, and C–C Cleavage Reactions

2023

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Selective azidation−amination of long-chain alkanoyl halobenzenes with sodium azide, promoted by copper(I) chloride, is reported. The protocol is, apart from CuCl and NaN 3 , additive free and allows the isolation of versatile amine−azides. Alkyl cleavage occurs as a side reaction through an unusual Schmidt-type azide insertion adjacent to the carbonyl group, forming alkyl nitriles possibly via radical pathways. Mechanistic studies involving 15 N labeling experiments and test substrates indicate that the reaction occurs via 1-azido-4-alkanoyl benzenes. The amination is applicable for substrates with electron-withdrawing groups and proceeds under mild conditions. The mechanism of the amine formation involves nitrenes. Intermediates were trapped by carrying out the reaction in the presence of the 2,2,6,6-(tetramethylpiperidin-1-yl)oxyl stable radical and characterized by high-resolution mass spectrometry. The intermediates are consistent with earlier mechanistic proposals.

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Section: Introductionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

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Copper(I) Chloride Mediated Amination of Halobenzenes via Azides: Scope, Mechanistic Aspects, and C–C Cleavage Reactions

2023

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“…So-formed electrodeposited layers are suitable to serve as anchoring points to immobilize catalytic compounds, e.g., enzymes [ 7 ] or metal nanoparticles [ 8 ], allowing the formation of heterogeneous catalysts applicable in sensors/biosensors [ 9 , 10 ], as well as electrochemical [ 8 , 11 , 12 ] or chemical reactions [ 13 ]. In recent years, several review articles describing the use of electrografting processes for the immobilization of catalysts have been published [ 14 , 15 ]. However, to the best of our knowledge, no one before has attempted to estimate the stability of those catalysts in practice.…”

Section: Introductionmentioning

confidence: 99%

Catalyst Design through Grafting of Diazonium Salts—A Critical Review on Catalyst Stability

Smołka,

Krukiewicz

2023

IJMS

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In the pursuit of designing a reusable catalyst with enhanced catalytic activity, recent studies indicate that electrochemical grafting of diazonium salts is an efficient method of forming heterogeneous catalysts. The aim of this review is to assess the industrial applicability of diazonium-based catalysts with particular emphasis on their mechanical, chemical, and thermal stability. To this end, different approaches to catalyst production via diazonium salt chemistry have been compared, including the immobilization of catalysts by a chemical reaction with a diazonium moiety, the direct use of diazonium salts and nanoparticles as catalysts, the use of diazonium layers to modulate wettability of a carrier, as well as the possibility of transforming the catalyst into the corresponding diazonium salt. After providing descriptions of the most suitable carriers, the most common deactivation routes of catalysts have been discussed. Although diazonium-based catalysts are expected to exhibit good stability owing to the covalent bond created between a catalyst and a post-diazonium layer, this review indicates the paucity of studies that experimentally verify this hypothesis. Therefore, use of diazonium salts appears a promising approach in catalysts formation if more research efforts can focus on assessing their stability and long-term catalytic performance.

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Catalysed Aryl Amine Syntheses via Azides: From Azidation of Aryl Halides to Azide Reduction and Direct Amination

Roemer

2024

ChemCatChem

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This review summarises and discusses aryl amine and azide syntheses from aryl halides employing azides. The majority of the reported reactions proceed with copper catalysis or mediation. Often, an aryl azide is formed in the first step, which is then reduced in situ to an aryl amine in a second step. The occurrence of the second step, the reduction, depends on the chosen reaction conditions and the substrates. The formation of only aryl azides through Cu‐mediated C–N bond formations is discussed, followed by mediated and catalytic aryl azide reduction employing different catalytic systems, and azidation with in situ azide reduction to amines, viz. azidation‐amination strategies. The azidation‐amination allows for the synthesis of complex heterocycles in multi‐step one‐pot procedures, of which several are summarised here. Examples of the application of azidation‐amination for synthesising important aryl amines employed in or as biologically active compounds, catalysis and materials science are also summarised. Finally, conducted control reactions have been collected and discussed in combination with mechanistic proposals. This literature survey allows us to pinpoint design criteria for the azide reduction to valuable amines, which includes the choice of reaction conditions such as solvent system and additives, involved metal and promising substrates.

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On the Use of Diazonium Salts in the Design of Catalytic Hybrid Materials and Coatings

Cited by 3 publications

References 77 publications

Copper(I) Chloride Mediated Amination of Halobenzenes via Azides: Scope, Mechanistic Aspects, and C–C Cleavage Reactions

Copper(I) Chloride Mediated Amination of Halobenzenes via Azides: Scope, Mechanistic Aspects, and C–C Cleavage Reactions

Catalyst Design through Grafting of Diazonium Salts—A Critical Review on Catalyst Stability

Catalysed Aryl Amine Syntheses via Azides: From Azidation of Aryl Halides to Azide Reduction and Direct Amination

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