Boryl Acrylaldehyde: An Elusive Member of the -Boryl Aldehyde Class of Reagent

We describe a synthetic route to boryl acrylaldehyde, anamphoteric molecule that features BMIDA and aldehyde functionalitiesattached to an sp(2)-carbon center. As the project unfolded, conventionalprotocols based on aldol condensation turned out to be unsuccessful.We eventually zeroed in on oxidative conditions that preserved the BMI-DA group and delivered the desired aldehyde functionality. During our investigation, it became clear that boryl alcohol displays hemilabile N-Bbonding, which differs dramatically from the previously described congeners with the sp(3)-carbon center connected to boron. We have at-tempted to understand the origins of this behavior using DFT calculations. Overall, boryl acrylaldehyde can be considered as an attractiveentry point in synthetic methods. These studies are underway in ourlaboratory