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Palladium‐Catalyzed Sc(OTf)3/Cs2CO3‐Assisted C−O Cross‐Coupling of Vinylidenecyclopropane‐Diesters with Phenolic Compounds.
- Source :
-
Advanced Synthesis & Catalysis . 8/6/2024, Vol. 366 Issue 15, p3387-3396. 10p. - Publication Year :
- 2024
-
Abstract
- 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. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 16154150
- Volume :
- 366
- Issue :
- 15
- Database :
- Academic Search Index
- Journal :
- Advanced Synthesis & Catalysis
- Publication Type :
- Academic Journal
- Accession number :
- 179110357
- Full Text :
- https://doi.org/10.1002/adsc.202400486