4.5 Article

CO2-Assisted Stereocontrolled Multi-Component Coupling Reactions Promoted by Ni-Catalytic System

Journal

ASIAN JOURNAL OF ORGANIC CHEMISTRY
Volume 11, Issue 10, Pages -

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ajoc.202200232

Keywords

carbon dioxide; dimethylzinc; multi-component coupling reaction; nickel catalyst; vinyl epoxide

Funding

  1. JSPS [JP22H02080]
  2. MEXT [18H04266]

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The combination of Ni-catalyst and PPh3 promotes a three-component coupling reaction of vinyl epoxide, alkyne, and dimethylzinc under a carbon dioxide atmosphere, leading to the formation of 2,5-heptadienyl alcohols with excellent E-stereoselectivity. The stereochemistry of the products is controlled through the formation of an oxanickelacycle intermediate via the insertion of carbon dioxide.
A combination of Ni-catalyst and PPh3 promotes the three-component coupling reaction of vinyl epoxide, alkyne, and dimethylzinc under a carbon dioxide atmosphere to provide 2,5-heptadienyl alcohols with excellent E-stereoselectivity. The stereochemistry of the products from the multi-component coupling reaction is controlled via an oxanickelacycle intermediate, which is formed by the insertion of carbon dioxide.

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