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Updated: Oct 7, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Cationic Iridium-Catalyzed Asymmetric Decarbonylative Aryl Addition of Aromatic Aldehydes to Bicyclic Alkenes
Reina Nonami1, Yusei Morimoto1, Kazuya Kanemoto2
1Department of Social Design Engineering National Institute of Technology, Kochi College, 200-1 Monobe Otsu, Nankoku, Kochi, 783-8508, Japan.
Abstract:
We report an unprecedented catalytic protocol for the enantioselective decarbonylative transformation of aryl aldehydes. In this process, the decarbonylation of aldehydes catalyzed by chiral iridium complexes enabled the formation of asymmetric C-C bonds through the formation of an aryl-iridium intermediate. The decarbonylative aryl addition to bicyclic alkenes was fluidly performed without a stoichiometric aryl-metal reagent, such as aryl boronic acid, with a cationic iridium complex generated in situ from Ir(cod)2 (BArF 4 ) and the sulfur-linked bis(phosphoramidite) ligand ((R,R)-S-Me-BIPAM). This reaction has broad functional group compatibility, and no waste is generated, except carbon monoxide.
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