Recent Advances in Catalysis Using Organoborane-Mediated Hydride Abstraction
Rebecca L. Melen, Louis C. Morrill, Alexander P. Pulis, Joseph P. Gillions, Salma A. Elsherbeni, Laura Winfrey, Yun Lei
Abstract
Abstract C–H functionalization is widely regarded as an important area in the development of synthetic methodology, enabling the design of more time- and atom-efficient syntheses. The ability of electron-deficient organoboranes to mediate hydride abstraction from α-amino C–H bonds is therefore of great interest, as the reactive iminium and hydridoborate moieties generated are able to participate in a range of synthetically useful transformations. In this review, we cover the recent advances made in organoborane-mediated hydride abstraction, and focus on the catalytic applications of electron-deficient boranes in α- or β-functionalization, α,β-difunctionalization, and the dehydrogenation of amines. 1 Introduction 2 α-Functionalization of Amines 3 β-Functionalization of Amines 4 α,β-Difunctionalization of Amines 5 Dehydrogenation of Amines 6 Summary and Future Prospects