Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 44, Pages 14580-14584Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201712520
Keywords
allylation; C-H activation; carboxylic acids; reaction mechanisms; ruthenium
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Funding
- Alexander von Humboldt Foundation
- DFG [EXC/1069, SFB/TRR 88]
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A carboxylate-directed ortho-C-H functionalization has been developed and it allows the regiospecific introduction of allyl residues to benzoic acids. In the presence of a [Ru(p-cymene)Cl-2](2) and K3PO4, benzoic acids react with allyl acetates at only 50 degrees C to give the corresponding ortho-allylbenzoic acids. The protocol is generally applicable to both electron-rich and electron-poor benzoic acids in combination with linear and branched allyl acetates. The products can be further functionalized in situ, for example, by double-bond migration, lactonization, or decarboxylation.
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