Journal ArticleDOI
Dimethylformamide as a carbon monoxide source in fast palladium-catalyzed aminocarbonylations of aryl bromides
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TLDR
The carbonylation procedure reported herein, which relies on the in situ generation of carbon monoxide, serves as a convenient alternative to othercarbonylation methods and is particularly applicable to small-scale reactions where short reaction times are desired and the direct use of carbonmonoxide gas is impractical.Abstract:
Dimethylformamide (DMF) acts as an efficient source of carbon monoxide and dimethylamine in the palladium-catalyzed aminocarbonylation (Heck carbonylation) of p-tolyl bromide to provide the dimethylamide. Addition of amines to the reaction mixture in excess delivers the corresponding aryl amides in good yields. The amines employed, benzylamine, morpholine, and aniline, all constitute good reaction partners. The reaction proceeds smoothly with bromobenzene and more electron-rich aryl bromides, but electron-deficient aryl bromides fail to undergo aminocarbonylation. The reactions are conducted at 180-190 degrees C for 15-20 min with microwave heating in a reaction mixture containing imidazole and potassium tert-butoxide: the latter is required to promote decomposition of the DMF solvent at a suitable rate. The beneficial effects of controlled microwave irradiation as an energy source for the rapid heating of the carbonylation reaction mixture are demonstrated. The carbonylation procedure reported herein, which relies on the in situ generation of carbon monoxide, serves as a convenient alternative to other carbonylation methods and is particularly applicable to small-scale reactions where short reaction times are desired and the direct use of carbon monoxide gas is impractical.read more
Citations
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Journal ArticleDOI
Controlled microwave heating in modern organic synthesis.
TL;DR: This Review highlights recent applications of controlled microwave heating in modern organic synthesis, and discusses some of the underlying phenomena and issues involved.
Journal ArticleDOI
Palladium-catalyzed carbonylation reactions of aryl halides and related compounds.
TL;DR: The recent academic developments in palladium-catalyzed carbonylation reactions of aromatic halides in the presence of various nucleophiles are summarized and the first industrial processes are summarized.
Journal ArticleDOI
Design, Synthesis, Structure, and Gas (N2, Ar, CO2, CH4, and H2) Sorption Properties of Porous Metal-Organic Tetrahedral and Heterocuboidal Polyhedra
TL;DR: A strategy based on assembling metal ions and organic carboxylate links has been applied for the design and synthesis of a new class of porous, truncated tetrahedral and heterocuboidal polyhedra, whose pore size and functionality can be systematically varied.
Journal ArticleDOI
Evolution of carbonylation catalysis: no need for carbon monoxide.
Tsumoru Morimoto,Kiyomi Kakiuchi +1 more
TL;DR: This minireview describes carbonylation reactions that can be conducted without the direct use of carbon monoxide, which provide reliable and accessible tools for synthetic organic chemists.
References
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Journal ArticleDOI
Chelate-assisted, Pd-catalyzed efficient carbonylation of aryl chlorides
Journal ArticleDOI
A More Efficient Catalyst for the Carbonylation of Chloroarenes
TL;DR: The right ligand enables the efficient carbonylation of unactivated chloroarenes and a general synthesis of benzoic acid derivatives is possible with the palladium-ferrocenylphosphane catalysts.
Journal ArticleDOI
Synthesis of primary aromatic amides by aminocarbonylation of aryl halides using formamide as an ammonia synthon.
Anita Schnyder,Matthias Beller,Gerald Mehltretter,Thomas Nsenda,Martin Studer,Adriano Indolese +5 more
TL;DR: Primary aromatic amides were prepared by a palladium-catalyzed aminocarbonylation reaction of aryl halides in high yields inHigh yields (70-90%) using formamide as the amine source using N-methylformamide and N,N-dimethylformamide asTheAmine source.
Journal ArticleDOI
Migrations of the Trimethylsilyl Group upon Electron Impact in Steroids
Journal ArticleDOI
Direct observation of .beta.-hydride elimination reactions on metal surfaces
TL;DR: Mise en evidence d'un mecanisme par elimination en β dhydrure dans la decomposition d'hydrocarbures sur des surfaces metalliques as mentioned in this paper.
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