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Nickel-Catalyzed -Carboxylation of Ynamides with Carbon Dioxide

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Title: Nickel-Catalyzed -Carboxylation of Ynamides with Carbon Dioxide
Authors: Doi, Ryohei Browse this author
Okano, Taichi Browse this author
Abdullah, Iman Browse this author
Sato, Yoshihiro Browse this author →KAKEN DB
Keywords: ynamides
carbon dioxide
nickel catalysis
β-amino acids
Issue Date: Jun-2019
Publisher: Georg Thieme Verlag
Journal Title: Synlett
Volume: 30
Issue: 9
Start Page: 1048
End Page: 1052
Publisher DOI: 10.1055/s-0037-1611529
Abstract: A nickel-catalyzed -selective hydrocarboxylation of ynamides to give protected dehydro--amino acids was developed. The key to exclusive -selectivity was the use of diethylzinc as a reductant in the presence of a magnesium salt. The reaction was conducted with bis(acetylacetonato)nickel(II) instead of costly and sensitive bis(1,5-cyclooctadiene)nickel(0). In addition, the optimized ligand was inexpensive 1,5-cyclooctadiene. Investigation of the substrate scope revealed that both nitrogen and alkyne substituents have marked effects on the reaction efficiency. We obtained experimental clues that indicated the formation of a vinylzinc intermediate that forms a C-C bond with CO (2) .
Type: article (author version)
Appears in Collections:薬学研究院 (Faculty of Pharmaceutical Sciences) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

Submitter: 土井 良平

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