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Ruthenium(II)-Catalyzed Cyclization of Aromatic Acids with Allylic Acetates via Redox-Free Two-Fold Aromatic/Allylic C-H Activations: Combined Experimental and DFT Studies
, Jambu S., Tamizmani M.
Published in ACS Publications
2018
Volume: 20
   
Issue: 7
Pages: 1982 - 1986
Abstract
A Ru(II)-catalyzed, redox-free, two-fold aromatic/allylic C-H bond activation of aromatic acids with allylic acetates to give (Z)-3-ylidenephthalides is described. In the reaction, H2 was formed as a side product. The detailed mechanistic investigation and DFT studies including the transition-state analysis support the postulate that the C-H allylation takes place at the ortho position of aromatic acids with allylic acetates followed by intramolecular cyclization at the allylic C(sp3)-H via a π-allylruthenium intermediate. © 2018 American Chemical Society.
About the journal
JournalOrganic Letters
PublisherACS Publications
Open AccessNo