Abstract
A mild, cascade type methodology was developed for the synthesis of polyphenolic ethers by the palladium-catalyzed cross coupling of phenols and halo compounds under microwave heating. In most cases, reactions run in neat conditions and in some cases, IPA/water mixture, and 1,4-dioxane were employed as solvents to furnish the products. By applying this new method, we were able to synthesize and purify a good number of polyether compounds with complete spectral data.
Highlights
The transformation of simple phenols into a platform of polyphenolic ethereal structure offers an extremely powerful tool in organic synthesis
A mild, cascade type methodology was developed for the synthesis of polyphenolic ethers by the palladium-catalyzed cross coupling of phenols and halo compounds under microwave heating
We found that PdCl2(dppf)CH2Cl2 shows effective catalytic effect for this new transformation
Summary
The transformation of simple phenols into a platform of polyphenolic ethereal structure offers an extremely powerful tool in organic synthesis. Phenolic compounds are present in medicinal and edible plants such as; flavonoids, chalcones, coumarins, quinones, phenolic acids [1]-[7]. The antioxidant potential of phenolic compounds shows potent activities for cancer prevention and its treatment. We report a novel route for phenolic ethers based on a cascade type reaction consisting of phenols and trihalo and dihalo compounds. The pioneer works of transition metal catalyzed cross-coupling reactions for C-O bonds done by Buchwald and Hartwig are well cited in the literature. In 1996, Buchwald and coworkers published an article about the synthesis of oxygen heterocycles using palladium catalyst to create C-O bonds [8]. Buchwald introduced a new biarylphosphine ligand with [(cinnamyl)PdCl]2 complex for the successful
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