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Updated: Sep 12, 2025

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
Naphthylpyridyl-Cu(II)-Catalyzed Oxidative Coupling of 2-Naphthylamines to Access BINAM Derivatives
Jonghyeon Lee1, Jooyeon Lee1, Minwoo Kong1,2
1Department of Chemistry, Chungbuk National University, Chungdae-ro 1, Seowon-gu, Cheongju 28644, South Korea.
Abstract:
In this study, we report the efficient synthesis of 1,1'-binaphthyl-2,2'-diamine (BINAM) derivatives via copper-catalyzed oxidative coupling of 2-aminonaphthalenes. The use of a ligand featuring an extended π system in combination with Cu(II) and molecular oxygen as the terminal oxidant enabled the formation of various BINAM derivatives in yields of up to 84%. Mechanistic investigations suggest a redox pathway involving Cu(II)/Cu(I) cycling, and π-π interactions between the ligand and substrate are proposed to stabilize reactive intermediates, thereby contributing to the observed efficiency.
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