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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Patent
Method for catalyzing carbonyl amination reaction of aryl halide by using graphene-loaded nano-palladium
TL;DR: In this article, a method for catalyzing a carbonyl amination reaction of aryl halide by using graphene-loaded nano-palladium is presented, which conforms to the synthesis concept of environmental protection and has a great application prospect in the field of catalysis.
Journal ArticleDOI
Pd(triNHC)‐catalyzed Double Carbonylation of Aryliodides With Amines: The Effect of triNHC Ligands
Baji Shaik,Hye-Young Jang +1 more
Book ChapterDOI
Applications of sonochemistry and microwaves in organometallic chemistry
TL;DR: In this paper, the authors describe the chemical applications of ultrasound and microwaves in the synthesis of organometallic compounds in their own right, as precursors to advanced materials and in accelerating organic syntheses.
Journal ArticleDOI
Photoassisted Charge Transfer Between DMF and Substrate: Facile and Selective N,N-Dimethylamination of Fluoroarenes.
Tharique N. Ansari,Sudripet Sharma,Pranjal P. Bora,Deborah Ogulu,Saurav Parmar,Fabrice Gallou,Pawel M. Kozlowski,Sachin Handa +7 more
TL;DR: In this paper, a reversible Van der Waals complex formation between the electron-deficient fluorinated aromatic ring and N,N-dimethylformamide (DMF) molecules followed by light irradiation resulted in charge transfer (CT) process.
References
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Journal ArticleDOI
Progress in hydroformylation and carbonylation
TL;DR: The last 15 years of hydroformylation and carbonylation chemistry are reviewed in this article, including technical and commercial aspects, and the authors present a review of the most relevant papers.
Journal ArticleDOI
Developments in Microwave-Assisted Organic Chemistry
TL;DR: The CSIRO continuous microwave reactor (CMR) and microwave batch reactor (MBR) were developed for organic synthesis and operated at temperatures up to 200°C (1400 kPa) and 260°C(10 MPa) respectively as discussed by the authors.
Journal ArticleDOI
Microwave-assisted high-speed chemistry: a new technique in drug discovery.
Mats Larhed,Anders Hallberg +1 more
TL;DR: It is believed that the time saved by using focused microwaves is potentially important in traditional organic synthesis but could be of even greater importance in high-speed combinatorial and medicinal chemistry.
Journal ArticleDOI
Microwave-Promoted Palladium-Catalyzed Coupling Reactions
Mats Larhed,Anders Hallberg +1 more
Journal ArticleDOI
Fast Microwave-Assisted Preparation of Aryl and Vinyl Nitriles and the Corresponding Tetrazoles from Organo-halides
Mathias Alterman,Anders Hallberg +1 more
TL;DR: A very potent HIV-1 protease inhibitor (K(i) = 0.
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