| Organoboranes are currently one of the most important synthetic intermediates used in organic synthesis. They are often used in C-C coupling reactions and are also prepared relatively straightforward using the hydroboration reaction. This reaction provides high yields and excellent regioselectivity. One of the issues of the hydroboration reaction is that it provides regioisomers in which the boron will attach to the primary or the secondary position of an alkene dependent on steric and electronics effects of the substrate. Due to current analytical methods and techniques, analyzing organoborane regioisomers could be a tedious process and highly time consuming. Herein we have developed a new method that utilizes both the coordination of organoboranes with 11B NMR spectroscopy in order to separate and detect the various compositions of regioisomers from a hydroboration reaction. In doing so, we are also able to calculate the regioselectivity of the reaction with a simple addition of a ligand that can potentially reduce the analytical time of organoboranes from an average of 2 days down to 15 minutes after the reaction. This new method will open doors to the way we understand trialkylboranes and their magnetic environments and hopefully some day be extended as an analytical tool for various organoborane derivatives. |
