Metal-free reductions of C–O bonds utilizing highly Lewis acidic boron catalysts and stoichiometric silane reductants has gained significant attention over the past years. One of the more challenging substrates for this class of reductions include amides due to their high Lewis basicity. Herein we present the mild and chemoselective reduction of secondary and tertiary amides utilizing novel, easily synthesized highly Lewis acidic boron catalysts. Factors determining the selectivity of the process and applications towards the reduction of peptides and biologically active compounds will be discussed. Furthermore, this system offers a convenient platform for the facile generation of a diverse catalyst library. Efforts towards the development of such a library and its impact on the chemoselective reduction of complex molecules will be described.

Metal-free chemoselective amide reductions utilizing novel Lewis acidic boron catalysts

255th National Meeting (2018)

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