Direct conversion of raw materials to fine chemicals is greatly economically influential. We developed a non-expensive cobalt-catalyzed multicomponent carbonylative reaction for the synthesis of γ-aryl carboxylic acid esters from readily available methylarene, ethylene, and CO, which are widely found in multiple FDA-approved drugs.
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Cobalt-Catalyzed Carbonylative Synthesis of 4-Oxobutanoates from Formamide and Ethylene.
Org Lett
October 2023
Dalian National Laboratory for Clean Energy, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 116023 Dalian, Liaoning, China.
The direct concurrent installation of amide and ester groups across olefin motifs represents a powerful and promising functionalization tool in organic chemistry. Herein, a ligand-free cobalt-catalyzed four-component radical relay carbonylative difunctionalization of ethylene for the synthesis of 4-oxobutanoates has been developed. Valuable C4 building blocks were produced in a highly atom-economical fashion.
View Article and Find Full Text PDFCobalt-Catalyzed Four-Component Carbonylation of Methylarenes with Ethylene and Alcohols.
J Org Chem
May 2022
Dalian National Laboratory for Clean Energy, Dalian Institute of Chemical Physics, Chinese Academy of Science, 116023 Dalian, Liaoning, China.
Direct conversion of raw materials to fine chemicals is greatly economically influential. We developed a non-expensive cobalt-catalyzed multicomponent carbonylative reaction for the synthesis of γ-aryl carboxylic acid esters from readily available methylarene, ethylene, and CO, which are widely found in multiple FDA-approved drugs.
View Article and Find Full Text PDFCobalt- and rhodium-catalyzed carboxylation using carbon dioxide as the C1 source.
Beilstein J Org Chem
September 2018
Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto 615-8510, Japan.
Carbon dioxide (CO) is one of the most important materials as renewable chemical feedstock. In this review, the Co- and Rh-catalyzed transformation of CO via carbon-carbon bond-forming reactions is summarized. Combinations of metals (cobalt or rhodium), substrates, and reducing agents realize efficient carboxylation reactions using CO.
View Article and Find Full Text PDFCarboxyzincation Employing Carbon Dioxide and Zinc Powder: Cobalt-Catalyzed Multicomponent Coupling Reactions with Alkynes.
J Am Chem Soc
May 2016
Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto 615-8510, Japan.
Cobalt-catalyzed carboxyzincation reactions employing carbon dioxide and zinc metal powder are developed. By using alkynes as substrates, regio- and stereodefined (Z)-β-zincated acrylates are provided. The corresponding alkenylzinc moiety can be converted to various substituents, affording multisubstituted acrylic acids.
View Article and Find Full Text PDFA four-component reaction involving in situ generated organometallic reagents: straightforward access to β-amino esters.
Chemistry
April 2013
Electrochimie et Synthèse Organique, Institut de Chimie et des Matériaux Paris-Est, UMR 7182 CNRS-Université Paris-Est Créteil Val de Marne, 2-8 rue Henri Dunant, 94320 Thiais, France.
Four in one: A straightforward synthesis of β(2,3)-amino esters is described through a new zinc-mediated, cobalt-catalyzed four-component reaction between organic bromides, alkyl acrylates, amines, and aldehydes (see scheme). Synthesis involves a Mannich-related conjugate addition/aza-aldol domino sequence, allowing the formation of three single bonds in one step. A reaction mechanism, emphasizing the crucial role of zinc salts, is described.
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