Cobalt(iii)-catalyzed redox-neutral [4+2]-annulation of N-chlorobenzamides/acrylamides with alkylidenecyclopropanes at room temperature?

Chemical Communications Pub Date: 2021-03-09 DOI: 10.1039/D1CC00654A

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.

Graphical abstract: Cobalt(iii)-catalyzed redox-neutral [4+2]-annulation of N-chlorobenzamides/acrylamides with alkylidenecyclopropanes at room temperature
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