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  • Title: Cobalt(iii)-catalyzed redox-neutral [4+2]-annulation of N-chlorobenzamides/acrylamides with alkylidenecyclopropanes at room temperature.
    Author: Ramesh B, Jeganmohan M.
    Journal: Chem Commun (Camb); 2021 Apr 18; 57(30):3692-3695. PubMed ID: 33725082.
    Abstract:
    An efficient synthesis of substituted 3,4-dihydroisoquinolinones through [4+2]-annulation of N-chlorobenzamides/acrylamides having a monodentate directing group with alkylidenecyclopropanes in the presence of a less expensive, highly abundant and air stable Co(iii) catalyst via a C-H activation is demonstrated. In this reaction, the N-Cl bond of N-chlorobenzamide serves as an internal oxidant and thus an external metal oxidant is avoided. The 3,4-dihydroisoquinolinone derivatives are converted successfully into the highly useful imidoyl chloride derivatives. The deuterium labeling and kinetic isolabelling studies reveal that the C-H activation is a rate-determining step in this cyclization reaction.
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