Organic Letters p. 1966 - 1973 (2021)
Update date:2022-07-29
Topics:
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
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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