Deoxygenation of Alcohols Employing Water as the Hydrogen Atom Source

摘要

This report provides evidence that water-trialkylborane solvent mixtures, in the absence of metal hydrides, are capable of mediating the deoxygenation of xanthate esters, perhaps through the intermediacy of trialkylborane-water complexes. These results not only represent a potentially useful alternative to available methods for replacing alcohols with hydrogen, deuterium, or potentially tritium but also suggest more broadly the existence of a novel mode of reactivity for water. In this regard, the analogy of trialkylborane-water complexes to metal-water complexes seen in biological systems (e.g., photosystem Ⅱ) is particularly intriguing. Further investigations into the mechanistic details of this deoxygenation and other uses of triakylborane aqua complexes are currently in progress.