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A direct α-Csp³-H methylenation of arylketones to form C-C bond using dimethyl sulfoxide as one-carbon source is achieved under transition metal-free reaction condition. Various aryl ketone derivatives react readily with DMSO, producing the α,β-unsaturated carbonyl compounds in yields of 42 to 90%. This method features a transition metal-free reaction condition, wide substrate scope and using DMSO as novel one-carbon source to form C-C bond, thus providing an efficient and expeditious approach to an important class of α,β-unsaturated carbonyl compounds. Based on the preliminary experiments, a plausible mechanism of this transformation is disclosed. [ABSTRACT FROM AUTHOR]

A novel K2S2O8-promoted decarboxylative cross coupling of α,β-unsaturated carboxylic acids with cyclic ethers was developed under aerobic conditions. The present protocol, which includes C-C and CO bond formation in one step through addition, oxidation, and decarboxylation processes, leads to the desired ketone products in moderate to excellent yields. In addition, mechanism studies showed that the transformation process undergoes a radical pathway via a direct activation of the α-sp³ C-H bond of oxygen of the cyclic ether. [ABSTRACT FROM AUTHOR]