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Aryl Ethers From Arenediazonium Tetrafluoroborate Salts: From Neat Reactions To Solvent-Mediated Effects, James A. Shriver, Daniel P. Flaherty, Cameron C. Herr

Journal of the Iowa Academy of Science: JIAS

A general procedure for the synthesis of various aryl ethers via the thermal decomposition of benzenediazonium tetrafluoroborate salts is described. Studies performed in neat alcohol at 60°C gave aryl ethers in yields ranging from 0-73%. Upon completion of a series of reactions, the effect of solvent was explored to expand the scope and relevance of this procedure. It was found that even solvents that are traditionally non-nucleophilic gave rise to products including bi-aryls and N-aryl acetamides. The utilization of an ionic liquid, l-butyl-4-methylpyridinium tetrafluoroborate, resulted in yields comparable to reactions performed in neat alcoholic solvents.