Search results for "Aryl halide"
showing 10 items of 10 documents
Synthesis of 1,3-bis(trimethylcyclam) and 1,3-bis(trimethylcyclen) substituted benzenes
2009
Pd-catalyzed amination of 1,3-dibromobenzene with N,N',N''-trimethylcyclam and N,N',N''-trimethylcyclen provided corresponding 1,3-bis(tetraazamacrocyclic) derivatives of benzene in 25-32% yields. The dependence of the products yields on the phosphine ligand applied (BINAP, DavePHOS) as well as on the stoichiometry of starting compounds was established. Scope and limitations for the synthesis of N-phenyl and N-(3-bromophenyl) derivatives of trimethylcyclam and trimethylcyclen were demonstrated.
Stabilized Naked Sub-nanometric Cu Clusters within a Polymeric Film Catalyze C-N, C-C, C-O, C-S, and C-P Bond-Forming Reactions
2015
[EN] Sub-nanometric Cu clusters formed by endogenous reduction of Cu salts and Cu nanoparticles are active and selective catalysts for C−N, C−C, C−O, C−S, and C−P bond-forming reactions. Sub-nanometric Cu clusters have also been generated within a polymeric film and stored with full stability for months. In this way, they are ready to be used on demand and maintain high activity (TONs up to 104 ) and selectivity for the above reactions. A potential mechanism for the formation of the sub-nanometric clusters and their electronic nature is presented.
Ready Access to Proquinazid Haptens via Cross-Coupling Chemistry for Antibody Generation and Immunoassay Development.
2015
17 pages, 4 tables, 5 figures.-- Publisher's PDF
Multiple Roles of Isocyanides in Palladium-Catalyzed Imidoylative Couplings: A Mechanistic Study
2016
International audience; Kinetic, spectroscopic and computational studies examining a palladium-catalyzed imidoylative coupling highlight the dual role of isocyanides as both substrates and ligands for this class of transformations. The synthesis of secondary amides from aryl halides and water is presented as a case study. The kinetics of the oxidative addition of ArI with RNC-ligated Pd-0 species have been studied and the resulting imidoyl complex [(ArC=NR)Pd(CNR)(2)I] (Ar=4-F-C6H4, R = tBu) has been isolated and characterized by X-ray diffraction. The unprecedented ability of this RNC-ligated imidoyl-Pd complex to undergo reductive elimination at room temperature to give the amide in the p…
Palladium-Catalysed Intermolecular Direct C–H Bond Arylation of Heteroarenes with Reagents Alternative to Aryl Halides: Current State of the Art
2022
Abstract: This unprecedented review with 322 references provides a critical up-to-date picture of the Pd-catalysed intermolecular direct C–H bond arylation of heteroarenes with arylating reagents alternative to aryl halides that include aryl sulfonates (aryl triflates, tosylates, mesylates, and imidazole-1-sulfonates), diaryliodonium salts, [(diacetoxy)iodo]arenes, arenediazonium salts, 1-aryltriazenes, arylhydrazines and N’-arylhydrazides, arenesulfonyl chlorides, sodium arenesulfinates, arenesulfinic acids, and arenesulfonohydrazides. Particular attention has been paid to summarise the preparation of the various arylating reagents and to highlight the practicality, versatility, and limit…
Heterogeneously catalyzed Suzuki-Miyaura conversion of broad scope
2012
The reaction tolerates a broad range of functional groups in the coupling partners and is usually performed in solution under homogeneous conditions at T ¢ 60 uC using 2–3 mol% catalytic amounts. The catalyst is often a Pd(0) complex with triarylphosphane ligands. 2 The catalytic cycle (Scheme 2) begins with the oxidative addition of an aryl halide to a Pd(0) species formed in situ to form an arylpalladium(II) halide intermediate. 3 Chloroarenes, especially nonactivated aryl chlorides, are notoriously less reactive due to the stability of the C–Cl bond (the relative reactivity of Ar–X is correlated to the respective bond dissociation energy: Ph–Cl: 96 kcal mol 21 ,P h–Br: 81 kcal mol 21 ,P …
Solid state halogen bonded networks vs. dynamic assemblies in solution: explaining N⋯X interactions of multivalent building blocks
2015
Tetrapyridine functionalized resorcinarene macrocycles were used as multivalent building blocks for the construction of halogen bonded networks with aryl halide linkers. In the solid state, resorcinarene macrocycles and aryl halide linker molecules assembled into interpenetrated, multidimensional halogen bonded networks with porous structure caused by the 3D block scaffold of the resorcinarenes. 19F NMR spectroscopy proved halogen bond formation also in solution, as either upfield or downfield shifts were observed depending on the bivalent or monovalent halogen bond binding mode. The binding mode in solution was explained by density functional theory computations. peerReviewed
Electrosynthesis as a powerful method for the generation of catalytic intermediates: efficient isolation of a palladium aryl halide oxidative additio…
2011
International audience; Polyphosphane ligands of controlled conformation promote highly efficient palladium-catalyzed cross-coupling reactions. Electrosynthesis has been used as a new straightforward method to obtain important intermediates in the search for a better mechanistic understanding. As a proof of concept, the facile synthesis of a phenyl iodopalladium(II) complex (2) was conducted at the electrolysis scale from a readily electrogenerated unstable Pd0 precursor.
ChemInform Abstract: Eco-Friendly Functionalization of Natural Halloysite Clay Nanotube with Ionic Liquids by Microwave Irradiation for Suzuki Coupli…
2014
Abstract Microwave assisted halloysite (HNT) external surface functionalization with ionic liquids is described. HNTs modification was achieved in two steps: a) grafting of 3-mercaptopropyl trimethoxysilane on the external surface of HNT by a microwave irradiation; b) anchorage of vinylimidazolium ionic liquids by a thiol-ene reaction. MW irradiation allowed us to obtain high loading onto the HNT surface compared to those obtained through conventional synthesis. Fourier transform infrared spectroscopy and thermogravimetric analysis confirmed that the grafting has occurred only on the external surface of HNT. Turbidimetric and dynamic light scattering analyses showed that the introduction of…
Eco-friendly functionalization of natural halloysite clay nanotube with ionic liquids by microwave irradiation for Suzuki coupling reaction
2014
Abstract Microwave assisted halloysite (HNT) external surface functionalization with ionic liquids is described. HNTs modification was achieved in two steps: a) grafting of 3-mercaptopropyl trimethoxysilane on the external surface of HNT by a microwave irradiation; b) anchorage of vinylimidazolium ionic liquids by a thiol-ene reaction. MW irradiation allowed us to obtain high loading onto the HNT surface compared to those obtained through conventional synthesis. Fourier transform infrared spectroscopy and thermogravimetric analysis confirmed that the grafting has occurred only on the external surface of HNT. Turbidimetric and dynamic light scattering analyses showed that the introduction of…