Fluorinated Alcohols

Fluorinated Aliphatic Alcohols and Diols

Fluorinated Aromatic Alcohols and Phenols

Introduction

Fluorinated alcohols have attracted extensive research attention due to their low boiling point, high melting point, high polarity, strong hydrogen bonding and strong solubility. A large number of fluorinated alcohols were developed and used. In organic synthesis, they can be used to obtain new organic fluorinated products with high yield and selectivity. In addition, they are also very important pharmaceutical intermediates and are widely used in the synthesis of fluorine-containing pharmaceuticals such as anesthetics, antirheumatic pharmaceuticals and antibacterial pharmaceuticals.

Applications

As important fluorinated building blocks, fluorinated alcohols are widely used in the organic synthesis and pharmaceuticals.

• Organic synthesis. Fluorinated alcohols are widely used in organic synthesis to synthesize a series of new organic fluorides. For example, Wu's group used readily available fluorinated alcohols as hydroxyfluoroalkylation reagents to form various α-aryl-α-trifluoromethyl alcohols. Specifically, in the presence of 2,2,6,6-tetramethyl-1-piperidinyloxyl (TEMPO), they started from cheap and easily accessible fluorinated alcohols and arenes to synthesized a series of α-aryl-α-trifluoromethyl alcohols through Ru(II)-catalysis. Wu's group provided a facile and mild method for the synthesis of α-aryl-α-trifluoromethyl alcohols^[1].

Fig.1 Synthesis of α-aryl-α-trifluoromethyl alcohols from fluorinated alcohols

• Pharmaceuticals. In addition to being used in organic synthesis, fluorinated alcohols are also used in the synthesis of many pharmaceuticals. For example, 2,2,2-trifluoroethanol (TFE) can be used in the synthesis of anesthetics desflurane, isoflurane, etc. 1,1,1,3,3,3-Hexafluoroisopropanol (HFIP) can synthesize sevoflurane, an inhalation anesthetic. Besides, fluorinated phenols are also widely used in the synthesis of pharmaceuticals, and a series of anti-rheumatic pharmaceuticals, enzyme inhibitors, etc. have been synthesized by fluorinated phenols. For example, p-fluorophenol can be used to synthesize the non-steroidal anti-inflammatory analgesics sulindac and the aldose reductase inhibitor sorbinil. 2,4-Difluorophenol can be used to synthesize the dopamine β-hydroxylase inhibitor etamicastat.

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Reference

1. Wu, Y. S.; et al. Ruthenium-catalyzed ortho-C-H hydroxyfluoroalkylation of arenes with fluorinated alcohols. J. Org. Chem. 2022, 87(21): 14364-14373.