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  • Title: Cobalt-Catalyzed Asymmetric Migratory Nozaki-Hiyama-Kishi Coupling.
    Author: Chen J, Wu L, Song Z, Wang Y, Li Z, Wang Y, Zhu S.
    Journal: J Am Chem Soc; 2024 Sep 25; 146(38):26223-26232. PubMed ID: 39284303.
    Abstract:
    Selective functionalization of ubiquitous C-H bonds based on 1,n-metal migration provides an attractive and sustainable route to access complex molecules from readily available precursors. Herein, we report a Co-catalyzed asymmetric reductive migratory Nozaki-Hiyama-Kishi (NHK) coupling between two readily available electrophiles, aryl (pseudo)halides and aldehydes, via an unprecedented through-space aryl-to-alkenyl 1,4-cobalt/hydride shift. The judicious choice of ligands is crucial for selectivity, leading to either ipso- or migratory NHK products with exquisite control of regio-, E/Z-, and enantioselectivity. Enabled by a ligand relay catalytic strategy, this platform has been further extended to aryl-to-aryl asymmetric migratory NHK coupling. These high-value NHK adducts, including α-chiral allylic alcohols and benzyl alcohols, are readily convertible to a variety of useful synthons.
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