Synthesis of aromatic aldehydes via silver(I)-catalyzed formylation of aryl bromides in DMF promoted by samarium metal in air

Abstract

Under ambient temperature conditions, a novel method has been developed for the conversion of aryl bromides to aromatic aldehydes, utilizing DMF (N,N-dimethylformamide) as both the starting material and solvent, in the presence of samarium metal and a trace of silver salts. This research has successfully explored an efficient approach for Barbier-type addition reactions, leading to the establishment of a novel C-C bond. A variety of bromides have been investigated as substrates, and aldehydes are readily obtained in moderate to high yields under mild conditions. The presence of 1 mol% of silver nitrate and potassium iodide is sufficient to catalyze the reaction, with the primary role of potassium iodide being to generate soluble silver iodide in the organic solvent, thereby catalyzing the reaction. The mechanism of the silver(I)-catalyzed process is discussed.