Formose Reaction Controlled by a Copolymer of N,N-Dimethylacrylamide and 4-Vinylphenylboronic Acid

The formose reaction is an oligomerization of formaldehyde under basic conditions, which produces a complicated mixture of monosaccharides and sugar alcohols. Selective formation of useful monosaccharides by the formose reaction has been an important challenge. In this study, we have investigated the formose reaction controlled by N,N-dimethylacrylamide/4-vinylphenylboronic acid copolymer (pDMA/VBA) and phenylboronic acid (PBA) because boronic acid compounds form esters with polyols, e.g., monosaccharides and sugar alcohols. We obtained time–conversion data in the presence of these boronic acid compounds, and characterized the products by liquid chromatography-mass spectroscopy and NMR measurements. pDMA/VBA and PBA decelerated the formose reaction because of the formation of boronic acid esters with products. It is noteworthy that the formose reaction in the presence of pDMA/VBA and PBA formed favorably six- and seven-carbon branched monosaccharides and sugar alcohols.