Zirconium-catalyzed Nagata reaction for the synthesis of 2-aryl-1,3,2-aryldioxaborins via a mild three-component condensation of phenols, aldehydes, and boronic acid

✍ Scribed by Hongchao Zheng; Dennis G. Hall

• Publisher: Elsevier Science
• Year: 2010
• Tongue: French
• Weight: 431 KB
• Volume: 51
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/j.tetlet.2010.06.035

✦ Synopsis

An efficient ZrCl 4 catalyzed ortho-hydroxyalkylation of phenols with aldehydes promoted by 3,5-bis (trifluoromethyl)phenyl boronic acid, leading to the formation of 2-aryl-1,3,2-aryldioxaborins was investigated and optimized. The reaction afforded the desired aryldioxaborins in good to excellent yields under mild conditions at room temperature. The electron-deficient boronic acid promoter was essential. Electron-rich phenols react faster, and both alkyl and aryl aldehydes are suitable substrates. The resulting aryldioxaborins can be further elaborated to produce substituted saligenols, 2-ethoxy chromans and 2-substituted phenols.