Premium
Regioselective C−H Alkylation via Carboxylate‐Directed Hydroarylation in Water
Author(s) -
Zhang Guodong,
Jia Fan,
Gooßen Lukas J.
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201800757
Subject(s) - alkylation , regioselectivity , chemistry , derivatization , carboxylate , benzoic acid , catalysis , medicinal chemistry , acrylic acid , base (topology) , organic chemistry , combinatorial chemistry , copolymer , high performance liquid chromatography , polymer , mathematical analysis , mathematics
In the presence of catalytic [RuCl 2 ( p ‐cym)] 2 and using Li 3 PO 4 as the base, benzoic acids react with olefins in water to afford the corresponding 2‐alkylbenzoic acids in moderate to excellent yields. This C−H alkylation process is generally applicable to diversely substituted electron‐rich and electron‐deficient benzoic acids, along with α,β‐unsaturated olefins including unprotected acrylic acid. The widely available carboxylate directing group can be removed or utilized for further derivatization. Mechanistic investigations revealed that the transformation proceeds via a ruthenacycle intermediate.