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
Addition of carbamoylsilane to isatins: Highly efficient synthesis of 3-hydroxy-3-aminocarbonyl-2-oxindoles derivatives
TL;DR: The first addition reaction between isatins and carbamoysilane has been developed which provides 3-hydroxy-3-aminocarbonyl-2-oxindoles core structures with excellent yields.
Journal ArticleDOI
Catalytic Carbonylation Methods without the Direct Use of Carbon Monoxide
TL;DR: In this paper, a review describes innovative strategies to solve the drawbacks of carbon monoxide carbonylation chemistry and provides many synthetic organic chemists with experimentally simple and safe tools for carbononylation.
Book ChapterDOI
Carbonylation and decarbonylation reactions
TL;DR: This chapter presents important recent advances in carbonylation chemistry, including decarbonylative coupling reactions, which are also useful in organic synthesis.
Book ChapterDOI
Hydroxy-, Alkoxy- and Aminocarbonylations of C–X Bonds
Matthias Beller,Xiao-Feng Wu +1 more
TL;DR: In this paper, transition metal catalyzed carbonylative activation of C-X bonds with nucleophiles such as water, alcohols or amines are called hydroxy carbonyaltion, alkoxy carbonylation or aminocarbonylation, respectively.
Journal ArticleDOI
Carbon Nitride Photoredox Catalysis Enables the Generation of the Dioxolanyl Radical for Conjugate Addition Reactions
TL;DR: Graphitic carbon nitride (g-C3N4) is used as photocatalyst in the Giese reaction of dioxolane and a wide variety of electron-deficient olefins as discussed by the authors .
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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