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
Aminocarbonylations of alkenyl phosphates, chlorides, bromides, and triflates with Mo(CO)6 as a solid CO source
TL;DR: Palladium-catalyzed aminocarbonylations of alkenyl chlorides, bromides, and triflates were investigated using Mo(CO)6 as a solid carbon monoxide source as mentioned in this paper.
Journal ArticleDOI
Microwave assisted, palladium catalyzed aminocarbonylations of heteroaromatic bromides using solid Mo(CO)6 as the carbon monoxide source
Michael A. Letavic,Kiev S. Ly +1 more
TL;DR: In this article, the direct conversion of a variety of heteroaromatic bromides into hetero-aromatic amides using microwave heating is described, which utilizes Mo(CO) 6 as the carbon monoxide source and allows for very short reaction times.
Journal ArticleDOI
Pd-catalyzed Heck cyclization and in situ hydrocarboxylation or hydromethenylation via a hydrogen borrowing strategy
Xianglei Liu,Zhenhua Gu +1 more
TL;DR: In this article, a Pd-catalyzed hydrocarboxylation of the in situ formed neopentylic alkenes by the use of "borrowed hydrogen" from Heck-type β-hydride elimination was reported.
Journal ArticleDOI
Copper-Catalyzed Coupling of Indoles with Dimethylformamide as a Methylenating Reagent
Fan Pu,Yang Li,Yong-Hong Song,Jianliang Xiao,Jianliang Xiao,Zhong-Wen Liu,Chao Wang,Zhao-Tie Liu,Jian-Gang Chen,Jian Lu +9 more
TL;DR: In this paper, the copper-catalyzed CH activation of indole was demonstrated as an efficient and facile protocol for synthesizing 3,3′-diindolylmethane (DIM) and its derivatives.
Journal ArticleDOI
Potential Safety Hazards Associated with Using N,N-Dimethylformamide in Chemical Reactions
TL;DR: N,N-Dimethylformamide (DMF) is frequently used as a solvent because of its unique physical properties that allow it to solubilize both organic and inorganic substances as discussed by the authors.
References
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Journal ArticleDOI
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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
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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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