Generation of (amino)(boryloxy)carbenes from carbamoylboranes and their coupling reaction with aldehydes.

Carbamoylboranes were found to react with various aldehydes under heating conditions to give α-hydroxycarboxamides in good yields. A DFT study supports the mechanism, which involves thermally generated (amino)(boryloxy)carbene intermediates. To our knowledge, this is the first report on the generation of (amino)(boryloxy)carbene intermediates from carbamoylboranes and its application to carbon-carbon bond-forming reactions.