Formose reaction controlled by boronic acid compounds

Beilstein J Org Chem. 2016 Dec 8:12:2668-2672. doi: 10.3762/bjoc.12.263. eCollection 2016.

Abstract

Formose reactions were carried out in the presence of low molecular weight and macromolecular boronic acid compounds, i.e., sodium phenylboronate (SPB) and a copolymer of sodium 4-vinylphenylboronate with sodium 4-styrenesulfonate (pVPB/NaSS), respectively. The boronic acid compounds provided different selectivities; sugars of a small carbon number were formed favorably in the presence of SPB, whereas sugar alcohols of a larger carbon number were formed preferably in the presence of pVPB/NaSS.

Keywords: boronic acid compounds; formose reaction; sodium 4-vinylphenylboronate/sodium 4-styrenesulfonate copolymer; sodium phenylboronate; sugar alcohols; sugars.