Enantioselective CO2 Fixation Via a Heck-Coupling/Carboxylation Cascade Catalyzed by Nickel |
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Authors: | Alessandro Cerveri Riccardo Giovanelli Davide Sella Riccardo Pedrazzani Prof. Magda Monari Dr. Olalla Nieto Faza Prof. Carlos Silva López Prof. Marco Bandini |
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Affiliation: | 1. Dipartimento di Chimica “Giacomo Ciamician”, Alma Mater Studiorum – Università di Bologna, Via Selmi 2, 40126 Bologna, Italy;2. Departamento de Química Orgánica, Universidade de Vigo, As Lagoas (Marcosende), 36310 Vigo, Spain |
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Abstract: | A novel asymmetric nickel-based procedure has been developed in which CO2 fixation is achieved as a second step of a truncated Heck coupling. For this, a new chiral ligand has been prepared and shown to achieve enantiomeric excesses up to 99 %. The overall process efficiently furnishes chiral 2,3-dihydrobenzofuran-3-ylacetic acids, an important class of bioactive products, from easy to prepare starting materials. A combined experimental and computational effort revealed the key steps of the catalytic cycle and suggested the unexpected participation of Ni(I) species in the coupling event. |
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Keywords: | asymmetric catalysis carbon dioxide carboxylation cross-coupling nickel |
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