Fluorinated Carbonyl Compounds

Fluorinated Ketones

Fluorinated Diketones

Fluorinated Aldehydes

Fluorinated Esters

Fluorinated Amides

Fluorinated Lactones

Introduction

Fluorinated carbonyl compounds are important fluorinated building blocks in organic synthesis. They can be prepared through Diels-Alder reaction, Michael addition or Robinson annulation, and are widely used to construct alkenes, alkanes, heterocyclic compounds, etc. Since the introduction of fluorine atoms into carbonyl compounds can enhance lipid solubility and bioavailability, fluorinated carbonyl compounds are also widely used in the synthesis of bioactive molecules and drugs. At present, the synthesis and application of fluorinated carbonyl compounds have become one of the research hotspots of researchers.

Typical Fluorinated Carbonyl Compounds And Their Applications

There are many kinds of fluorinated carbonyl compounds, mainly including fluorinated ketones, fluorinated diketones, fluorinated aldehydes, fluorinated esters, fluorinated amides and fluorinated lactones.

• Fluorinated ketones. Fluorinated ketones can be used as building blocks for the synthesis of other organic compounds and are widely used in organic synthesis reactions. They can be used as starting materials for the synthesis of new compounds or as intermediates. Fluorinated ketones are also used in drug synthesis. For example, p-fluoroacetophenone can be used to synthesize certain anti-cancer drugs, such as cabazitaxel, which is used to treat prostate cancer and other types of cancer. p-Fluoroacetophenone can also be used to synthesize some antipsychotic drugs such as flupentixol, sedative drugs such as fluphenazine, and antidepressant drugs such as fluoxetine.
• Fluorinated diketones. Fluorinated diketones are one of the most popular structures in organic synthesis. There are many synthesis methods for them, including hydrolysis, oxidation, cycloaddition, etc. The most classic synthesis method is Claisen condensation. Fluorinated diketones also have a wide range of uses. They can undergo nucleophilic addition reactions, reduction reactions and hydrolysis reactions on the carbonyl group to obtain a series of alcohols, esters and carboxylic acid products.
• Fluorinated aldehydes. Fluorinated aldehydes are intermediates with broad application prospects. Due to the inductive effect of the strong electronegativity of the fluorine atom, the carbonyl groups on the fluorinated aldehydes are in an electron-deficient state. Compared with the ordinary aldehydes, the carbonyl groups on the fluorinated aldehydes are more vulnerable to the attack of the nucleophilic reagents. They can be used to prepare fluorine-containing carboxylic acids and fluorine-containing alcohols, and can also undergo Schiff base reactions with primary and secondary amines to modify amino-containing polymers.
• Fluorinated esters. Fluorinated esters are used in the synthesis of many bioactive molecules. For example, Li's group report a diastereoselective Mannich-type reaction of fluorinated esters with N-tert-butylsulfinyl imines. This method provides a powerful means to access a broad range of highly functionalized β-amino acids containing α-fluorinated quaternary stereogenic carbon centers^[1].

Fig.1 Synthesis of β-amino acids from fluorinated esters

• Fluorinated amides. Fluorinated amides participate in a variety of chemical reactions to obtain new organic fluorides. For example, Stanforth reported the Wittig reaction of fluorinated amides. Fluorinated amides reacted with phosphorane at room temperature giving a mixture of enamine and imine in excellent yields. Furthermore, the β-amino acid derivatives can be formed by reducing imines with sodium borohydride^[2].

Fig.2 Synthesis of enamines and imines from fluorinated amides

• Fluorinated lactones. Fluorinated lactones also play an important role in the synthetic chemistry. They are not only important synthetic building blocks of natural products, but also used to synthesize some fine chemical products and pharmaceutical intermediates.

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References

1. Li Y; et al. Diastereoselective Mannich-type reaction of α-fluorinated carboxylate esters: synthesis of β-amino acids containing α-quaternary fluorinated carbon centers. Org. Biomol. Chem. 2016, 14(27): 6457-6462.
2. Stanforth, S. P. The Wittig reaction of fluorinated amides: formation of enamine and imine tautomers. Tetrahedron. 2001, 57(9): 1833-1836.