Details

Autor(en) / Beteiligte

• Brittain, William D. G
• Cobb, Steven L

Titel

Tetrafluoropyridyl (TFP): a general phenol protecting group readily cleaved under mild conditionsElectronic supplementary information (ESI) available. CCDC 1856218-1856219. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c8ob02899k

Erscheinungsjahr

2019-02

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• Phenols are extremely valuable building blocks in the areas of pharmaceuticals, natural products, materials and catalysts. In order to carry out modifications on phenols, the phenolic oxygen is routinely protected to prevent unwanted side reactions. Presently many of the protecting groups available can require harsh conditions, specialist equipment, expensive or air/moisture-sensitive reagents to install and remove. Here we introduce the use of the tetrafluoropyridyl (TFP) group as a general protecting group for phenols. TFP can be installed in one step with no sensitivity to water or air, and it is stable under a range of commonly employed reaction conditions including acid and base. The TFP protecting group is readily cleaved under mild conditions with quantitative conversion to the parent phenol, observed in many cases in less than 1 hour. Herein we introduce tetrafluoropyridyl (TFP) as a new general protecting group for phenols. The TFP protecting group is readily cleaved under mild conditions.