Premium
Regioselective Threefold Aromatic Substitution of Benzoic Acid Derivatives by Dearomatization, Regioselective Functionalization, and Rearomatization
Author(s) -
Koch Eva,
Studer Armido
Publication year - 2013
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.201300259
Subject(s) - regioselectivity , alkylation , chemistry , benzoic acid , combinatorial chemistry , palladium , substitution (logic) , organic chemistry , catalysis , computer science , programming language
Ipso, meta, and para : Benzoic acid derivatives can be highly regioselectively substituted at the ipso, meta , and para positions. The reaction sequence comprises an alkylative Birch reduction, a 4‐alkylation, a palladium‐catalyzed γ‐arylation, and an oxidative rearomatization (see scheme). All the reactions are robust and experimentally easy to conduct.