1259663-52-9Relevant academic research and scientific papers
Synthesis of aryl ketones by palladium(II)-catalyzed decarboxylative addition of benzoic acids to nitriles
Lindh, Jonas,Sjoeberg, Per J. R.,Larhed, Mats
, p. 7733 - 7737 (2010)
An efficient, sustainable method for the preparation of aryl ketones from ortho-substituted benzoic acids proceeds through their decarboxylation to generate an aryl-palladium species, followed by addition to a nitrile and hydrolysis of the intermediate ketimine.
Palladium(II)-catalyzed decarboxylative heck arylations of acyclic electron-rich olefins with internal selectivity
Fardost, Ashkan,Lindh, Jonas,Sjoeberg, Per J. R.,Larhed, Mats
, p. 870 - 878 (2014/04/03)
Despite the recent emergence of decarboxylative C-C bond forming reactions, methodologies providing internally arylated electron-rich olefins are still lacking. We herein report on palladium(II)-catalyzed decarboxylative Heck arylations of linear electron-rich olefins with excellent selectivity for the internal position. The method allows a variety of electron-rich linear olefins to undergo arylation with ortho-functionalized aromatic carboxylic acids, including heterocycles. The reaction mechanism has been explored with ESI-MS studies to confirm previous findings, and to reveal the formation of a highly stable palladium complex as a result of the Heck product reacting with the catalyst.
Bronsted acidic ionic liquid accelerated halogenation of organic compounds with N-halosuccinimides (NXS)
Vrazic, Dejan,Jereb, Marjan,Laali, Kenneth K.,Stavber, Stojan
, p. 74 - 96 (2013/04/10)
The Bronsted-Acidic ionic liquid 1-methyl-3-(4-sulfobutyl) imidazolium triflate [BMIM(SO3H)][OTf] was demonstrated to act efficiently as solvent and catalyst for the halogenation of activated organic compounds with N-halosuccinimides (NXS) under mild conditions with short reaction times. Methyl aryl ketones were converted into a-halo and a,a-dihaloketones, depending on the quantity of NXS used. Ketones with activated aromatic rings were selectively halogenated, however in some cases mixtures of a-halogenated ketone and ring-halogenated ketones were obtained. Activated aromatics were regioselectively ring halogenated to give mono- and dihalo-substituted products. The [BMIM(SO3H)][OTf] ionic liquid (IL-A) was successfully reused eight times in a representative monohalogenation reaction with no noticeable decrease in efficiency. An effective halogenation scale-up in this IL is also presented. The reactivity trend and the observed chemo- and regioselectiivities point to an ET process in these IL-promoted halofunctionalization reactions.
