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Enantioselective CO 2 Fixation Via a Heck‐Coupling/Carboxylation Cascade Catalyzed by Nickel
Author(s) -
Cerveri Alessandro,
Giovanelli Riccardo,
Sella Davide,
Pedrazzani Riccardo,
Monari Magda,
Nieto Faza Olalla,
López Carlos Silva,
Bandini Marco
Publication year - 2021
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202101082
Subject(s) - nickel , heck reaction , enantioselective synthesis , catalysis , combinatorial chemistry , carboxylation , cascade , enantiomer , ligand (biochemistry) , chemistry , tandem , catalytic cycle , coupling (piping) , palladium , organic chemistry , materials science , chromatography , receptor , biochemistry , metallurgy , composite material
A novel asymmetric nickel‐based procedure has been developed in which CO 2 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.