C–H and N–H Bond Annulation of Benzamides with Isonitriles Catalyzed by Cobalt(III)

Published as part of the Special Topic Cobalt in Organic Synthesis

In memory of Prof. Shunsuke Murahashi for pioneering work in cobalt-catalyzed C–H bond functionalization

Abstract

A simple efficient, atom-economical procedure was developed for the cobalt-catalyzed C–H bond annulation of benzamides with isonitriles under mild conditions. The reaction tolerates a variety of functional group including heterocycles. Diverse 3-(alkylimino)-2-quinolin-8-yl-2,3-dihydro-1H-isoindol-1-ones were synthesized using isonitriles as the C1 source through C–H and N–H bond annulation via C–H bond activation in a ‘green’ solvent. Vinylamides were also used similarly with tert-butyl isonitrile to give 3-(tert-butylimino)-1-quinolin-8-yl-1H-pyrrol-2(5H)-ones.

Key words

cobalt - annulation - isonitrile - C–H activation - iminoisoindolinone

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