Palladium‐Catalyzed Sc(OTf)3/Cs2CO3‐Assisted C−O Cross‐Coupling of Vinylidenecyclopropane‐Diesters with Phenolic Compounds

We herein describe a method in the synthesis of aryl ether derivatives from a cross‐coupling reaction of vinylidenecyclopropane‐diesters (VDCP‐diesters) with commercially available phenolic compounds for the formation of C−O bond under palladium catalysis and assisted by Sc(OTf)3/Cs2CO3. This develo...

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Bibliographic Details
Published inAdvanced synthesis & catalysis Vol. 366; no. 15; pp. 3387 - 3396
Main Authors Zhong, Xian‐Hua, Long, Yong‐Jie, Wei, Yin, Shi, Min
Format Journal Article
LanguageEnglish
Published Heidelberg Wiley Subscription Services, Inc 06.08.2024
Subjects
a zwitterionic palladium species
Bromine compounds
Chemical reactions
Chemical synthesis
Cross coupling
C−O cross-coupling
Density functional theory
Deuterium
Diesters
Iodine
Palladium
palladium catalysis
Phenols
Reaction mechanisms
Sc(OTf)3/Cs2CO3-assisted
Substrates
vinylidenecyclopropane-diesters
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Summary:We herein describe a method in the synthesis of aryl ether derivatives from a cross‐coupling reaction of vinylidenecyclopropane‐diesters (VDCP‐diesters) with commercially available phenolic compounds for the formation of C−O bond under palladium catalysis and assisted by Sc(OTf)3/Cs2CO3. This developed transformation proceeds through a nucleophilic addition at the 2‐position of allenic moiety at 50 °C for 4.0 h and is compatible with substituents such as bromine, iodine and borate on the phenolic substrates via a zwitterionic π‐propargyl palladium species, affording the desired products in 29% to 95% isolated yields. A plausible reaction mechanism has been also proposed on the basis of control, deuterium labeling experiments and density functional theory (DFT) calculations.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202400486