The aryl–aryl coupling reaction of 1-naphthol with SnCl4 for 2,2′-binaphthol synthesis and its application to the biomimetic synthesis of binaphthoquinone isolated from Plumbago zeylanica

✍ Scribed by Iwao Okamoto; Hirohisa Doi; Eiichi Kotani; Tetsuya Takeya

• Book ID: 104230408
• Publisher: Elsevier Science
• Year: 2001
• Tongue: French
• Weight: 71 KB
• Volume: 42
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)00337-9

✦ Synopsis

A simple method for the direct synthesis of 2,2%-binaphthols was developed, utilizing aryl-aryl coupling reaction via electron donor-acceptor complexes of 1-naphthols with SnCl 4 . Heating of the complex in a sealed tube afforded the corresponding o-o coupling product in excellent yield. This method was utilized for a biomimetic synthesis of the binaphthoquinone, 3,3%-biplumbagin, isolated from Plumbago zeylanica.