132464-52-9Relevant academic research and scientific papers
Directed Ortho and Remote Metalation of Naphthalene 1,8-Diamide: Complementing SEAr Reactivity for the Synthesis of Substituted Naphthalenes
Jones, Christopher C. V.,Patel, Jignesh J.,Jansen-Van Vuuren, Ross D.,Ross, Gregory M.,Keller, Bernd O.,Sauriol, Francoise,Schatte, Gabriele,Johnson, Erin R.,Snieckus, Victor
, p. 1966 - 1973 (2021)
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.
Remote Aromatic Metalation. An Anionic Friedel-Crafts Equivalent for the Regioselective Synthesis of Condensed Fluorenones from Biaryl and m-Teraryl 2-Amides
Fu, Jian-min,Zhao, Bao-ping,Sharp, M. J.,Snieckus, V.
, p. 1683 - 1685 (2007/10/02)
Remote metalation (t-BuLi, LDA) of m-teraryl and biaryl amides (Scheme I) constitutes a short and convenient route to a variety of substituted and condensed fluorenones, including aza analogues (Table I) and the natural product, dengibsinin (6a, Scheme II).
