Palladium(II) acetate catalyzed acylative cleavage of cyclic and acyclic ethers under neat conditions

A Sequential One‐Pot Synthesis of Functionalized Esters and Thioesters through a Ring‐Opening Acylation of Cyclic Ethers and Thioethers

“…The crude mixture was then purified by column chromatography. Compounds 4a,[6a] 4g, 4k, 6a, 6d, & 6e are reported are reported.…”

“…One viable route for their synthesis is the ring opening of cyclic ethers with acid halides. Although, acylative cleavage of cyclic ethers with acid halides is known, in general, they require catalysts such as Lewis acids, lanthanide salts, palladium/platinum complexes,, SmI 2 etc. or high pressures with the exception of acyl iodides .…”

α-Diimine-Niobium Complex-Catalyzed Deoxychlorination of Benzyl Ethers with Silicon Tetrachloride

“…Metal halides have also been reported as reagents for ether cleavage to give alkyl halides, where the metal acts as a halogen transfer reagent. For example, bismuth can transfer a chlorine atom to 2-methyl- and 2,5-dimethyltetrahydrofurans, where the ring is preactivated with an acyl chloride (Figure a). , Numerous other acylative metal-catalyzed ring-opening reactions are known that rely on relieving ring strain, giving esters rather than completely deoxygenated products. , Tungsten hexachloride has been used to stoichiometrically cleave many ethers, including benzyl ether, to form alkyl chlorides (Figure d); a variety of other products including alcohols and overhalogenated compounds are invariably produced as well . Simple halogenating reagents such as trimethylsilyl iodide or concentrated hydrobromic or hydroiodic acid are generally effective (Figure b and c), but these aggressive reagents are typically required in excess and can form a variety of different products depending on the conditions used. ,, …”