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
Palladium-catalyzed synthesis of aldehydes from aryl iodides and acetic formic anhydride.
Journal ArticleDOI
Zn-Mediated Reduction of Oxalyl Chloride Forming CO and Its Application in Carbonylation Reactions.
TL;DR: An efficient protocol for the generation of carbon monoxide by Zn-mediated reduction of oxalyl chloride by applying this new procedure to various carbonylation reactions in the presence of a transition metal catalyst under mild conditions and with a stoichiometric amount of CO source.
Journal ArticleDOI
AIBN-initiated metal free amidation of aldehydes using N-chloroamines
TL;DR: In this paper, an efficient and environmentally benign amidation of aldehydes with N-chloroamines was developed using AIBN as an initiator, which offers a metal free and base free approach and is endowed with mild reaction conditions, high yields, and good functional group tolerance.
Journal ArticleDOI
Palladium-catalyzed alkoxycarbonylation of aryl halides with phenols employing formic acid as the CO source
TL;DR: In this paper, an efficient palladium-catalyzed alkoxycarbonylation of aryl halides with phenols has been developed, which proceeds smoothly under mild conditions and good functional group tolerance was observed.
Journal ArticleDOI
A Four-Component Reaction Strategy for Pyrimidine Carboxamide Synthesis.
TL;DR: This sequential 3SM-4CR strategy features inexpensive, readily available starting materials, green oxidants, as well as atom and step economy, and has potential applications in the pharmaceutical industry.
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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