Oxidation of BINOLs by Hypervalent Iodine Reagents: Facile Synthesis of Xanthenes and Lactones. Issue 21 (14th March 2022)

• Record Type: Journal Article
• Authors: Zhang, Huaiyuan; Wirth, Thomas
• Is Part Of: Chemistry. Volume 28:Issue 21(2022)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-03-14
• Subjects: BINOL -- hypervalent iodine reagents -- lactones -- oxidation -- xanthenes; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.202200181
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: Xanthene derivatives have broad applications in medicines, fluorescent probes, dyes, food additives, etc. Therefore, much attention was focused on developing the synthetic methods to prepare these compounds. Binaphthyl‐based xanthene derivatives were prepared through the oxidation of BINOLs promoted by the hypervalent iodine reagent iodosylbenzene (PhIO). Nine‐membered lactones were obtained through a similar oxidative reaction when iodoxybenzene (PhIO2 ) was used. Additionally, one‐pot reactions of BINOLs, PhIO and nucleophiles such as alcohols and amines were also investigated to provide alkoxylated products and amides in good to excellent yields. Abstract : The oxidation of BINOLs promoted by hypervalent iodine reagents is leading to binaphthyl‐based xanthenes and to nine‐membered lactones in high yields. In the presence of alcohols this method provides a new strategy for the synthesis of alkoxylated xanthene derivatives.