Fluorinated Aliphatic Cyclic Hydrocarbons

Fluorinated Aliphatic Cyclic Hydrocarbons

Introduction

Fluorinated aliphatic cyclic hydrocarbons are closed-chain hydrocarbons with properties of aliphatic compounds. They can be divided into fluorinated saturated alicyclic hydrocarbons and fluorinated unsaturated alicyclic hydrocarbons. The boiling point, melting point and relative density of fluorinated aliphatic cyclic hydrocarbons are higher than those of open-chain aliphatic hydrocarbons with the same number of carbon atoms. They can undergo halogenation and oxidation reactions. Small-ring fluorinated aliphatic cyclic hydrocarbons can undergo ring-opening reactions due to their special structure. By these chemical reactions, fluorinated aliphatic cyclic hydrocarbons can synthesize new organic fluorides, making them play an increasingly important role as fluorinated building blocks.

Synthesis

The following are selected typical synthesis methods of fluorinated saturated aliphatic cyclic hydrocarbons and fluorinated unsaturated aliphatic cyclic hydrocarbons.

• Synthesis of fluorinated saturated aliphatic cyclic hydrocarbons. The Glorius' group developed a synthetic strategy for fluorinated cycloalkanes. They achieved a highly selective hydrogenation of a broad scope of fluorinated arenes and heteroarenes through rhodium complex catalysis, offering convenient access to fluorinated cycloalkanes^[1].

Fig.1 Synthesis of fluorinated cycloalkanes through hydrogenation

• Synthesis of fluorinated unsaturated aliphatic cyclic hydrocarbons. The regioselective cycloaddition reaction is rapid, straightforward, and highly efficient, helping to generate the highly functionalized 4-membered ring (4MR) carbocycles. Moses' group synthesized a series of fluorinated cyclobutenes through cycloaddition reaction. They used ethene-1,1-disulfonyl difluoride (EDSF) and aryl acetylenes as starting materials to rapidly and regioselectively generate 26 unique 1,1-bissulfonylfluoride substituted cyclobutenes through [2+2] cycloaddition reaction^[2].

Fig.2 Synthesis of fluorinated cycloalkenes through [2+2] cycloaddition reaction

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References

1. Glorius, F.; et al. Hydrogenation of fluoroarenes: Direct access to all-cis-(multi)fluorinated cycloalkanes. Science. 2017, 357(6354): 908-912.
2. Moses, J. E.; et al. Ethene-1,1-disulfonyl difluoride (EDSF) for SuFEx click chemistry: Synthesis of SuFExable 1,1-bissulfonylfluoride substituted cyclobutene hubs. Angew. Chem. Int. Ed. 2023, 62, e202303916.