Perfluoroalkylated compounds are primarily characterized by outstanding chemical, biological inertness, intense hydrophobic and lipophobic effects. In contrast to the selectively fluorinated compouns( from a single F to a C2F5 group,somethimes also named " lightly fluorinated), Perfluoroalkylated and other highly fluorinated compounds are used more in materials science than in life science.
Many effective and innovative products for diagnosis and therapy have already been launched on the market, although the specific properties and synthetic techniques of perfluoroalkylation still remains underdeveloped today. These commercially available PFC-based products include: the PFC-stabilized,micrometer-size gas bubbles for injectable sound reflectors in diagnosis( e.g. F-octyl bromide, C8F17Br(kumiph06), has been approved by FDA for use as contrast agent for ultrasound imaging.); materials for Ophthamology and reconstructive surgery; "blood substitues for oxygen delivery to tissues; drugs & drug delivery systems, etc..
Numerous advances have been made for perfluoroalkylation reactions, in which a perfluoroalkyl group can be introuced into organic skeleton by neither of eletrophilic, radical and nucleophilic approaches. Kumidas selectively and preferably offers the following five families of perfluoroalkylating reagents and perfluoroalkylated building blocks:
1. Fits Reagents: FITS ( perFluoroalkyphenylIodoniumTrifluoromethaneSulfonate) reagents are of great importance for introduction of perfluoroalkyl groups to organic compounds in electrophilic perfluoroalkylation pathways.
2. Perfluoroalkyl Halides Reagents: Perfluoroalkyl Halides do not act as effective electrophilic perfluoroalkylation reagents, as might be expected by analogy with the reactivity of alkyl halides; Most of them reported in the process of synthesis are playing roles of nucleophilic perfluoroalkyating reagents for synthetic chemists.
3. Perfluoroalkyl Sulfonyl Fluorides Reagents: Perfluoroalkanosulfonyl fluorides (RfSO2F,such as kumiPF04,kumiPF05 and KumiPF06) are stable,non-toxic,moisture-tolerant and cost effective reagents. In industry, they have been widely empolyed as precursors for the synthesis of highly valued surfactants,pefluoroalkanesulfonic acid salt RfSO3M. Due to the excellent leaving ability of perfluorosulfonate anion(RfSO3-), RfSO2F has been explored and used as an excellent hydroxyl group-activating reagent for fluorination of alcohols to synthesize fluorides, for cyclodehydration of chiral vicinal diols, N-acylamino alcohols, ß-hydroxy sulfonamides and ß-hydroxy thioamides for the synthesis of epoxides and other heterocyclic compounds, for the preparation of acid-sensitive from the substrate of a,ß-unstaturated ketoximes, for dehydration of aldoximes to nitriles, and for the synthesis of diphenylphosphinate esters via the reaction of diphenylphosphine oxide with alcohols.
4. Perfluoroalkyl Trimethylsilanes Reagents: Perfluoroalkyl Trimethylsilanes are regarded with growing interests as equivalents of Gringard's reagents.
5. Perfluoroalkylated Building Blocks: A new family of Perfluoroalkyl-substituted ethylene carbonates (PFB-EC[kumiPF01],PFH-EC[kumiPF02],PFO-EC[kumiPF03]) are provided and used as functional electrolyte additives for high-voltage lithium-ion batteries.
Perfluoroalkylating Reagents Overview
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