An Electrophilic Approach to the Palladium-Catalyzed Carbonylative C–H Functionalization of Heterocycles

A palladium-catalyzed approach to intermolecular carbonylative C–H functionalization is described. This transformation is mediated by P^<i>t</i>Bu₃-coordinated palladium catalyst and allows the derivatization of a diverse range of heterocycles, including pyrroles, indoles, imidazoles, benzoxazoles, and furans. Preliminary studies suggest that this reaction may proceed via the catalytic formation of highly electrophilic intermediates. Overall, this provides with an atom-economical and general synthetic route to generate aryl-(hetero)­aryl ketones using stable reagents (aryl iodides and CO) and without the typical need to exploit pre-metalated heterocycles in carbonylative coupling chemistry

A Nickel-Based, Tandem Catalytic Approach to Isoindolinones from Imines, Aryl Iodides, and CO

We describe herein a modular nickel-catalyzed synthesis of isoindolinones from imines, aryl iodides, and CO. This reaction is catalyzed by Ni­(1,5-cyclooctadiene)₂ in concert with chloride salts and postulated to proceed via a tandem nickel-catalyzed carbonylation to form <i>N</i>-acyl iminium chloride salts, followed by a spontaneous nickel-catalyzed cyclization. A range of aryl iodides and imines have been found to be viable substrates in this reaction, providing a modular route to generate substituted isoindolinones with high atom economy