Synthesis of Methylene‐Bridged Bisnaphthalenes as Building Blocks for Push–Pull Substituted Pentacenes. Issue 47 (20th December 2017)

• Record Type: Journal Article
• Authors: Wagner, Frederic; Harms, Klaus; Koert, Ulrich
• Is Part Of: European journal of organic chemistry. Issue 47(2017)
• Page Start: 7107
• Page End: 7121
• Publication Date: 2017-12-20
• Subjects: Arenes -- Suzuki coupling -- C1 building blocks -- Homogeneous catalysis -- Bisnaphthalenes; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201701540
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : 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. Abstract : The regioselective synthesis of methylene‐bridged substituted bisnaphthalenes is reported. Successful Suzuki reactions were achieved by using naphthyl trifluoroborates and bromomethylnaphthalenes.