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Asymmetric metal-catalyzed C-H functionalization is a powerful strategy for the rapid generation of complex target molecules from simple precursors. While aryl (pseudo) halides have been used as electrophilic substrates in enantioselective Pd(0)-catalyzed syntheses of N-heterocycles, alternative partners for C-H functionalizations remain underexplored. Herein we describe the first application of ketene aminal phosphates as competent electrophiles in a Pd(0)-catalyzed desymmetrization. This transformation allowed the efficient synthesis of chiral isoindolines in a highly enantioselective fashion. Furthermore, intending to introduce sought-after perfluoroalkyl substituents, we explored intramolecular C-H functionalization of imidoyl chlorides resulting in the asymmetric preparation of previously inaccessible 1H-isoindoles. Tailored chiral monodentate ligands afforded high levels of enantioinduction in both transformations.
Paul Joseph Dyson, Mingyang Liu, Yelin Hu, Matthias Beller
Zhaowen Dong, Feng Zhou, Yujing Zhang
Alkynes are found in a multitude of natural or synthetic bioactive compounds. In addition to the capacity of these chemical motifs to impact the physicochemical properties of a molecule of interest, the well-established reactivity of alkynes makes them ...