Tetrahedron

SnCl 4-mediated oxidative biaryl coupling reaction of 1-naphthol and subsequent ring closure of 2, 2′-binaphthol to the dinaphthofuran framework

T Takeya, H Doi, T Ogata, T Otsuka, I Okamoto…

Index: Takeya, Tetsuya; Doi, Hirohisa; Ogata, Tokutaro; Otsuka, Tsuyoshi; Okamoto, Iwao; Kotani, Eiichi Tetrahedron, 2004 , vol. 60, # 30 p. 6295 - 6310

Full Text: HTML

Citation Number: 21

Abstract

A simple method for the direct synthesis of 2, 2′-binaphthols and dinaphtho [1, 2-b; 2′, 1′- d] furans under mild conditions was developed, utilizing a biaryl coupling reaction via electron donor–acceptor complexes of 1-naphthols with SnCl4. Heating of the complex in a sealed tube for (18–24 h) afforded the corresponding o–o coupled product in excellent yield. Prolonged reaction (56–65 h) under the same conditions afforded in high yield in one step ...