TY  - JOUR
A1  - Bramborg, Andrea
A1  - Linker, Torsten
T1  - Regioselective synthesis of alkylarenes by two-step ipso-substitution of aromatic dicarboxylic acids
JF  - European journal of organic chemistry
N2  - A strategy for the regioselective alkylation of arenes was developed, starting from commercially available and inexpensive terephthalic acid or naphthalene-1,4-dicarboxylic acid. The method entails a formal ipso-substitution of the carboxylate groups by a sequence of reductive alkylation under Birch conditions and subsequent acid-mediated rearomatization with loss of carbon monoxide and carbon dioxide. More than 20 different arenes with various side-chains were synthesized. With naphthalene-1,4-dicarboxylic acid as starting material, we were able to control the degree of alkylation by choosing the appropriate electrophile in the Birch reduction. Thus, bisalkylated naphthalenes and naphthoic acids became available chemoselectively. All reactions afforded a single regioisomer exclusively in high yields. Overall, aromatic dicarboxylic acids are suitable substrates for a two-step ipso-substitution that allows the selective synthesis of alkylated benzenes and naphthalenes.
KW  - Synthetic methods
KW  - Alkylation
KW  - Birch reduction
KW  - Arenes
KW  - Regioselectivity
Y1  - 2012
U6  - https://doi.org/10.1002/ejoc.201200823
SN  - 1434-193X
IS  - 28
SP  - 5552
EP  - 5563
PB  - Wiley-VCH
CY  - Weinheim
ER  -