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Synthesis of Methylene‐Bridged Bisnaphthalenes as Building Blocks for Push–Pull Substituted Pentacenes
Author(s) -
Wagner Frederic,
Harms Klaus,
Koert Ulrich
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201701540
Subject(s) - chemistry , naphthalene , methylene , nitro , aryl , heck reaction , coupling reaction , medicinal chemistry , combinatorial chemistry , organic chemistry , catalysis , alkyl
The use of cross‐coupling reactions for the synthesis of methylene‐bridged bisnaphthalenes bearing two nitro groups on one naphthalene and two amino groups on the other has been investigated. A Hauser–Heck reaction was used to prepare the substituted naphthalene building blocks. It was not possible to install a transmetallating function in the benzylic position due to side reactions with the nitro and the amino groups. A successful Suzuki reaction was achieved by using naphthyl trifluoroborates and bromomethyl naphthalenes. The resulting dinaphthyl methanes could be useful for the synthesis of push–pull substituted pentacenes.