Merging C–C σ-bond activation of cyclobutanones with CO2 fixation via Ni-catalysis

Lorenzo Lombardi; Alessandro Cerveri; Leonardo Ceccon; Riccardo Pedrazzani; Magda Monari; Giulio Bertuzzi; Marco Bandini

doi:10.1039/D2CC00149G

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Merging C–C σ-bond activation of cyclobutanones with CO₂ fixation via Ni-catalysis†

Lorenzo Lombardi,^ab Alessandro Cerveri,^a Leonardo Ceccon,^a Riccardo Pedrazzani,^ab Magda Monari,

^ab Giulio Bertuzzi*^ab and Marco Bandini

*^ab

Author affiliations

* Corresponding authors

^a Dipartimento di Chimica “Giacomo Ciamician”, Alma Mater Studiorum, Università di Bologna, via Selmi 2, Bologna 40126, Italy
E-mail: giulio.bertuzzi2@unibo.it, marco.bandini@unibo.it

^b Center for Chemical Catalysis – C3, Alma Mater Studiorum – Università di Bologna, via Selmi 2, Bologna, Italy

Abstract

A carboxylative Ni-catalyzed tandem C–C σ-bond activation of cyclobutanones followed by CO₂-electrophilic trapping is documented as a direct route to synthetically valuable 3-indanone-1-acetic acids. The protocol shows an adequate functional group tolerance and useful chemical outcomes (yield up to 76%) when AlCl₃ is adopted as an additive. Manipulations of the targeted cyclic scaffolds and a mechanistic proposal based on experimental evidence complete the investigation.

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DOI: https://doi.org/10.1039/D2CC00149G
Article type: Communication
Submitted: 10 Jan 2022
Accepted: 25 Feb 2022
First published: 25 Feb 2022
This article is Open Access

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Chem. Commun., 2022,58, 4071-4074

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Merging C–C σ-bond activation of cyclobutanones with CO₂ fixation via Ni-catalysis

L. Lombardi, A. Cerveri, L. Ceccon, R. Pedrazzani, M. Monari, G. Bertuzzi and M. Bandini, Chem. Commun., 2022, 58, 4071 DOI: 10.1039/D2CC00149G

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