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Open Access Exploitation of Unconventional Electrophiles in Enantioselective Pd(0)-Catalyzed C–H Functionalizations

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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.

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Keywords: ASYMMETRIC CATALYSIS; C–H FUNCTIONALIZATION; HETEROCYCLES; LIGAND DESIGN; PALLADIUM

Document Type: Research Article

Affiliations: 1: Ecole Polytechnique Fédérale de Lausanne, EPFL SB ISIC LCSA, BCH 4305, CH-1015 Lausanne, SCS-Metrohm Award for best oral presentation in Organic Chemistry 2: Ecole Polytechnique Fédérale de Lausanne, EPFL SB ISIC LCSA, BCH 4305, CH-1015 Lausanne;, Email: [email protected]

Publication date: April 1, 2019

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  • International Journal for Chemistry and Official Membership Journal of the Swiss Chemical Society (SCS) and its Divisions

    CHIMIA, a scientific journal for chemistry in the broadest sense, is published 10 times a year and covers the interests of a wide and diverse readership. Contributions from all fields of chemistry and related areas are considered for publication in the form of Review Articles and Notes. A characteristic feature of CHIMIA are the thematic issues, each devoted to an area of great current significance.

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