We have discovered a novel nickel(0)-catalyzed cyclization of N-benzoylaminals to form 3-substituted isoindolinones. This method relies on the use of catalytic nickel(0) and stoichiometric Lewis acid to obtain the desired isoindolinone products. This reaction likely proceeds via an a-amidoalkylnickel(II) intermediate, which then may cyclize via either an electrophilic aromatic substitution or an insertion pathway. This method enables benzoyl chloride, primary amine and aldehyde to be transformed to the isoindolinone core in an efficient two-step procedure.

Nickel(0)-catalyzed cyclization of <i>N</i>-benzoylaminals for isoindolinone synthesis

243rd National Meeting (2012)

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Nickel(0)-catalyzed cyclization of N-benzoylaminals for isoindolinone synthesis