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Nickel Catalyzed Carbonylation/Carboxylation Sequence via Double CO<sub>2</sub> Incorporation

Riccardo Giovanelli, Lorenzo Lombardi, Riccardo Pedrazzani, Magda Monari, Marta Castiñeira Reis, Carlos Silva López, Giulio Bertuzzi, Marco Bandini

2023Organic Letters17 citationsDOIOpen Access PDF

Abstract

High Resolution Image Download MS PowerPoint Slide A carbonylation–carboxylation synthetic sequence, via double CO 2 fixation, is described. The productive merger of a Ni-catalyzed cross-electrophile coupling manifold, with the use of AlCl 3, triggered a cascade reaction with the formation of three consecutive C–C bonds in a single operation. This strategy traces an unprecedented synthetic route to ketones under Lewis acid assisted carbon dioxide valorization. Computational insights revealed a unique double function of AlCl 3, and labeling ( 13 CO 2 ) experiments validate the genuine incorporation of CO 2 in both functional groups.

Topics & Concepts

CarbonylationChemistryCarboxylationNickelCatalysisSequence (biology)Combinatorial chemistryCarbon monoxideOrganic chemistryBiochemistryCarbon dioxide utilization in catalysisCO2 Reduction Techniques and CatalystsAsymmetric Hydrogenation and Catalysis