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Regiospecific ortho ‐C−H Allylation of Benzoic Acids
Author(s) -
Trita A. Stefania,
Biafora Agostino,
Pichette Drapeau Martin,
Weber Philip,
Gooßen Lukas J.
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201712520
Subject(s) - decarboxylation , chemistry , benzoic acid , carboxylate , medicinal chemistry , organic chemistry , double bond , catalysis
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 K 3 PO 4 , benzoic acids react with allyl acetates at only 50 °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.