Deoxygenation Using Alkyl Boranes

 

During our work towards a total synthesis of the Phomidrides, an unique method was found to accomplish a Barton-McCombie type deoxygenation. Triethylborane and trimethylborane were shown to deoxygenate an hindered tertiary alcohol under aerobic  conditions. Deuterium studies showed that the source of the hydrogen atom was water. This method is a significant impovement to the Barton-McCombie method which utilizes stoichiometric amounts of a tin reagent. Current work involves the appplication of this system to other radical mediated reactions.