Fluoroalkanes

Fluoroalkanes

Introduction

In fluorinated building blocks, fluoroalkanes are a class of very valuable compounds. Due to the high electronegativity of fluorine atoms, fluoroalkanes have many unique properties, such as excellent chemical stability, surface activity and temperature resistance. In recent years, fluoroalkanes have become one of the research hotspots in the fields of medicine, electronics, environmental protection, etc. With the continuous development of technology, the application prospects of fluoroalkanes will be broader.

Applications

Fluoroalkanes building blocks are used in the synthesis of fluorine-containing arenes. For example, Xiao et al. developed a nickel-catalyzed cross-coupling reaction between 1-bromo-1,1-difluoroalkanes and (hetero)arylborons to synthesize a series of difluoroalkylated arenes. In this reaction, two ligands (a bidentate bipyridinebased ligand, 4,4'-ditBu-bpy, and a monodentate pyridinebased ligand, DMAP) offer a highly efficient nickel-based catalytic system, allowing the rapid synthesis of difluoroalkylated arenes from fluoroalkanes under mild reaction conditions. In addition, the reaction also has excellent functional-group compatibility^[1].

Fig.1 Synthesis of difluoroalkylated arenes from fluoroalkanes

In additon, fluoroalkanes building blocks are also used in the synthesis of fluorine-containing heterocyclic compounds. For example, Shen's group and Luo's group used fluoroalkanes, amidines, and styrenes as raw materials to quickly construct fluorine-containing pyrimidine heterocyclic compounds through three-component cyclization. The reaction is facilitated by a copper catalyst (Cu(acac)₂), a base (triethylenediamine), and an oxidant (tert-butanol peroxide) to form three new C-C/C-N bonds and a new six-membered ring through a radical addition/oxidation/cyclization sequence in a one-pot manner. They employed fluoroalkane building blocks to efficiently and regioselectively synthesize a series of polyfluoroalkyl-substituted pyrimidine derivatives in moderate to good yields, providing new targets for drug synthesis and the synthesis of functional organic materials^[2].

Fig.2 Synthesis of polyfluoroalkyl-substituted pyrimidine derivatives from fluoroalkanes

Alfa Chemistry can offer various fluoroalkanes building blocks. You can click on our product list for a detailed view. At the same time, we also offer product customization according to customer's detailed requirements. If you are interested in our products, please feel free to contact us. We will be happy to provide you with support and services.

References

1. Xiao Y. L.; et al. Nickel-catalyzed difluoroalkylation of (hetero)arylborons with unactivated 1-bromo-1,1-difluoroalkanes. Angew. Chem. 2016, 128(19): 5931-5935.
2. Shen Z. L.; et al. Copper-catalyzed three-component cyclization of amidines, styrenes, and fluoroalkyl halides for the synthesis of modular fluoroalkylated pyrimidines. Chem. Commun. 2018, 54(21): 2615-2618.