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Updated: Nov 15, 2025

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
Directed Ortho and Remote Metalation of Naphthalene 1,8-Diamide: Complementing SAr Reactivity for the Synthesis of
Christopher C V Jones1, Jignesh J Patel1, Ross D Jansen-van Vuuren1
1Department of Chemistry, Queen's University, Kingston, ON K7L 3N6, Canada.
Abstract:
Mono- and dianion species of 1,8-naphthalene diamide 2 were generated under sec-BuLi/TMEDA conditions and trapped with a variety of electrophiles to give 2- and 2,7- substituted products 3 and 4. Using Suzuki-Miyaura cross-coupling, mono- and di-iodinated products were converted into the corresponding 2-aryl (5) and 2,7-diaryl (6) products, respectively. The amide-amide rotation barrier of 2 was established by VT NMR, and the structure of fluorenone structure 9, obtained by remote metalation, was secured.
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