Perfluoroalkylation Agents

Perfluoroalkylation Agents

Introduction

Perfluoroalkylation agents are one of the important methods to synthesize perfluoroalkyl organic compounds. Organic compounds containing perfluoroalkyl groups have very important applications in the fields of medicine, pesticides, and advanced materials due to their strong electronegativity and strong lipophilicity. At present, many perfluoroalkylation agents have been developed to introduce perfluoroalkyl groups into organic molecules, which are easy to operate and easy to obtain, and have become one of the research hotspots in organic synthetic chemistry.

Common Perfluoroalkylation Agents

Ruppert-Prakash agents, perfluoroalkyl organometallic agents and perfluoroalkylphenyl iodotrifluoromethanesulfonates (FITS agents) are commonly used perfluoroalkylation agents.

• Ruppert-Prakash agents. Ruppert-Prakash agents (TMSCF₃, TMSC₂F₅, and TMSC₃F₇) are a class of off-the-shelf, air-stable, and easy-to-handle perfluoroalkylation agents. These reagents can be converted into CF₃^-, C₂F₅^-, C₃F₇^-, undergo nucleophilic substitution or addition with a series of electrophilic substrates such as aldehydes, ketones, esters, enolates, perfluoroaromatic compounds, etc., to synthesize a range of different trifluoromethylated or pentafluoroethylated or heptafluoropropylated substituents.
• Perfluoroalkyl organometallic agents. Organometallic compounds with perfluoroalkyl groups represent a large class of perfluoroalkylation agents. Among them, perfluoroalkylation agents of lithium, magnesium, zinc, copper, and silver have been used for perfluoroalkylation reactions with various electrophiles. Perfluoroalkyl lithium agents are prepared by lithium-halogen exchange between lithium metal and perfluoroalkyl halides at low temperatures. Similarly, perfluoroalkyl grignard agents were prepared using magnesium-halogen exchange. Perfluoroalkyl copper agents are usually used in the reactions of alkyl halides and pseudohalides. Perfluoroalkyl zinc agents are often combined with some common nucleophilic perfluoroalkylation substrates such as aldehydes and ketones.
• FITS agents. FITS agents can undergo perfluoroalkylation reactions with various nucleophilic substrates such as alkenes, dienes, and alkynes. Among them, the reaction of FITS agents with enol silyl ethers can prepare a-perfluoroalkyl-substituted carbonyl compounds. This reaction is very important for the introduction of perfluoroalkyl groups in drugs and the synthesis of perfluoroalkylated analogs of natural products.

Fig.1 Commonly used perfluoroalkylating agents

Alfa Chemistry can offer various perfluoroalkylation agents. You can click on our product list for a detailed view. If you do not find the product you want, we also offer product customization according to customer's detailed requirements. Please contact us, if you are in need of assistance.