Development of Organic Transformations Based on Protodeboronation

Although protodeboronation has been considered as an uncontrollable side reaction in metal-catalyzed cross-coupling and/or a decomposition pathway of unstable organoboron compounds, the synthetic organic community has not recognized the importance of protodeboronation and the underlying mechanism, and thus few organic transformations have been developed based on the protodeboronation of organoboron compounds until recently. However, recently the synthetic community has started to understand the reactionmechanism and reaction parameters for protodeboronation, which enabled us to develop methods in which carbon-boron bonds in organoboron compounds can be converted into carbon-hydrogen bonds under mild conditions. Based on this finding several synthetic protocols have been developed recently. In this chapter, recent progress in the development of novel organic transformations based on protodeboronation will be described.