One-pot catalysis of dehydrogenation of cyclohexanones to phenols and oxidative Heck coupling: expedient synthesis of coumarins.
نویسندگان
چکیده
One-pot reactions leading to highly functionalized coumarins have been developed via a Pd(II)-catalyzed dehydrogenation-oxidative Heck-cyclization process.
منابع مشابه
Auto‐Tandem Catalysis: PdII‐Catalysed Dehydrogenation/Oxidative Heck Reaction of Cyclopentane‐1,3‐diones
A PdII catalyst system has been used to successfully catalyse two mechanistically distinct reactions in a one-pot procedure: dehydrogenation of 2,2-disubstituted cyclopentane-1,3-diones and the subsequent oxidative Heck coupling. This auto-tandem catalytic reaction is applicable to both batch and continuous flow processes, with the latter being the first example of a tandem aerobic dehydrogenat...
متن کاملSynthesis of novel tridentate ligand-based palladium catalyst and investigation of its reactivity towards Suzuki, Sonogashira and Heck coupling reactions
We have demonstrated a simple and efficient route for the synthesis of a novel imine based tridentate ligand and its Pd-complex to investigate the C-C cross-coupling reactions, that involve column chromatography purification in only one step. The catalytic activity of the newly synthesized catalyst was studied for the Suzuki, Sonogashira and, Heck cross-coupling reactions under mild conditions....
متن کاملReaction-activated palladium catalyst for dehydrogenation of substituted cyclohexanones to phenols and H2 without oxidants and hydrogen acceptors† †Electronic supplementary information (ESI) available: Experimental procedures and 1H and 13C NMR of new materials. See DOI: 10.1039/c5sc01044f Click here for additional data file.
It is widely believed that the dehydrogenation of organic compounds is a thermodynamically unfavorable process, and thus requires stoichiometric oxidants such as dioxygen and metal oxides or sacrificial hydrogen acceptors to remove the hydrogen from the reaction mixture to drive the equilibrium towards the products. Here we report a previously unappreciated combination of common commercial Pd/C...
متن کاملBrønsted acidic ionic liquid as the efficient and reusable catalyst for synthesis of coumarins via Pechmann condensation under solvent-free conditions
A mild and efficient method has been developed for the preparation of substituted coumarins from reaction of various phenols with different β-ketoesters via Pechmann condensation in the presence of Brønsted acidic ionic liquid (N-(4-sulfonic acid) butyl triethylammonium hydrogen sulfate) as an effective catalyst under solvent-free conditions. Different phenols reacted with ethyl acetoacetate to...
متن کاملPalladium-catalyzed aerobic dehydrogenation of substituted cyclohexanones to phenols.
Aromatic molecules are key constituents of many pharmaceuticals, electronic materials, and commodity plastics. The utility of these molecules directly reflects the identity and pattern of substituents on the aromatic ring. Here, we report a palladium(II) catalyst system, incorporating an unconventional ortho-dimethylaminopyridine ligand, for the conversion of substituted cyclohexanones to the c...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
عنوان ژورنال:
- Chemical communications
دوره 49 38 شماره
صفحات -
تاریخ انتشار 2013