TY  - JOUR
A1  - Krüger, Tobias
A1  - Vorndran, Katja
A1  - Linker, Torsten
T1  - Regioselective arene functionalization : simple substitution of carboxylate by alkyl groups
N2  - Arenes with various alkyl side-chains were synthesized in high yields and excellent regioselectivities. Starting from toluic and naphthoic acids, the carboxylate group was conveniently substituted by alkyl halides by Birch reduction and subsequent decarbonylation. The method is characterized by inexpensive starting materials and reagents, and methylation of arenes was realized. Besides simple alkyl substituents, the scope of arene functionalization was extended by benzyl, fluoro, amino, and ester groups. We were able to control the alkylation of 1-naphthoic acid during Birch reduction by the addition of tert-butanol. This allowed the regioselective synthesis of mono and bis-substituted naphthalenes from the same starting material.
Y1  - 2009
UR  - https://publishup.uni-potsdam.de/frontdoor/index/index/docId/31749
UR  - http://www3.interscience.wiley.com/cgi-bin/jhome/26293/
SN  - 0947-6539
ER  -