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Updated: Sep 18, 2025
Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
Regioselective Modification Distinguishing Slight Difference between Two C-Br Bonds in 1,7-Dibromonaphthalene and
Kento Iwai1,2, Nana Hatayama1, Akitaka Ito1
1School of Engineering Science, Kochi University of Technology, Tosayamada, Kami, Kochi 782-8502, Japan.
Abstract:
Dibromonaphthalenes are valuable building blocks in organic synthesis; however, achieving discrimination between the α- and β-bromo groups remains a challenge. In this study, we demonstrated the regioselective conversion of the bromo group in 1,7-dibromonaphthalene with high efficiency. Transition metal-catalyzed cross-coupling reactions with boronic acids or amines predominantly proceeded at the less hindered 7-position. Conversely, bromine-lithium exchange occurred at the 1-position. This selective functionalization strategy enables the synthesis of 1,7-disubstituted naphthalene with precise control, offering potential applications in developing functional materials.
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