Although the synthetic methodologies for the introduction of the pentafluoroethyl group(CF2CF3) into organic molecules are not clearly as developed as trifluoromethylation, impressive progress has been made in the field of pentafluoroethylation in the past few decades. The Pentafluoroethyl group(CF2CF3) is featuring some attractive and unique characteristics as a new substituent fo the future for synthetic chemists. Such advantages include: chemically stable and highly resistant to the action of P450 enzymes by leading to increased metabolic stability at sites where it is incorporated;Comparable lipophilicity to SF5( ClogP);Slightly less electronegative than SF5, Size intermediate between CF3 and t-butyl groups, etc..
Compared to CF3 ( by far the most common fluoroalkyl group) and SF5( super trifluoromethyl group), CF2CF3 group can bring a novel combination of localize electronegativity,lipophilicity and metabolic stability, which therefore leads to improvements in the overall effectiveness of target compunds. Many examples have already been reported of biologically active CF2CF3 derivatives that outperform their CF3 congeners, for instance, some valylprolylvalylpentafluoroethyl ketones have been found to act as active inhibitors of human neurophile elastase, whereas the corresponding CF3 analogue exhibit no activity. Much has been reported in recent years about SF5 group as the " substitue of the future"" by introducing the trioka of enhanced lipophility,electronegativey and metabolic stability into pharmaceutical and agrochemcial products. The SF5 functional group is offering an alternative pathway to the creation of new chemcial compounds with enhanced drug performance, which has clearly ledt o improved efficacy in a number of cases, such as Treatment of Alzheimer's disease (Astrazeneca),Antidiabetic agents(Schering Corporation),Treatment of ischemic disease(Sanofi-Aventis), Anti-cancer drugs( Hoffmanne-la Roche), Horticultural insecticide( Nippon Noyaku),Antiparasitic agents(Novartis, Pfizer), Parasiticides(Pfizer), and so on. However, the development of broader SF5-containing compounds with expected function improvements is still remaining limited up till now because it is difficult to incorporte a SF5 group into a propective drug compounds.
Given the clear need for new pentafluoroethylation methods, some well-defined pentafluoroethylating reagents have been developped. For example, Pentafluoroethyl Copper(CuCF2CF3,kumi5F03) and (Pentafluoroethyl)trimethylsilane(TMSCF2CF3,kumi5F02) was utilized as economical pentafluoroethyl sources in many applications. More recently, Harwig and his group developed a novel and shelf-stable reagent, Pentafluoroethylator( (bpy)CuCF2CF3,kumi5F04), for the rapid addition of a CF2CF3 group into almost any postion of most vinyl, aryl and heteroaryl compounds under mild conditions. In most recent, Trimethyl(trifluoromethyl)silane(TMSCF3,kumi3F01) can be reportedly utilized as a convenient source of CF2=CF2 for Pentafluoroethylation, which provides a new and efficient strategy for preparation of pentafluoroethylated compounds by fluoride addition to tetrafluoroethylene-containing synthon in a simple two-chamber system. This current strategy constitutes a new method for pentafluoroethylation,and thus may find applications in the synthesis of F-labeled CF3CF2 compounds.
Pentafluoroethylating Reagents Overview
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You can either buy our pentafluorethylating reagents and then introduce pentafluoroethyl group into your own desired compounds, or you can simply order the building blocks pre-loaded with the -CF2CF3 subsitituent.
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