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Relevant academic research and scientific papers

Addition Reactions of F-Alkyl Iodides to Carbon-Carbon Double Bonds Promoted by Metallic Tin(0)-Metal Salt System

F-Alkyl iodides readily reacted with a variety of alkenes in methanol at room temperature under the influence of metallic tin(0)-silver(I) acetate or metallic tin(0)-copper(I) chloride to afford the corresponding addition products, F-alkylated iodides, in

Indium-mediated radical addition of perfluoroalkyl iodide in water

Reaction of perfluoroalkyl groups with carbon-carbon unsaturated compounds using indium in water proceeded smoothly to provide the addition products in high yields.

Visible light promoted fluoroalkylation of alkenes and alkynes using 2-bromophenol as a catalyst

We report a new protocol for the fluoroalkylation of alkenes and alkynes by using 2-bromophenol as a catalyst. This reaction can be tailored for different reaction modes by altering the base and solvent, which feature a wide substrate scope and excellent functional group tolerance with high chemo- and regioselectivities. We further propose a mechanism involving an electron donor-acceptor (EDA) complex.

Radical Perfluoroalkylation Enabled by a Catalytically Generated Halogen Bonding Complex and Visible Light Irradiation

Exploiting charge-transfer complexes in visible light-promoted single-electron redox reactions is a promising route for opening novel synthetic pathways, and catalytic approaches to complex formation are critical for facilitating this chemistry. This report describes the use of a substituted hydroquinone catalyst to promote radical perfluoroalkylation reactions. Mechanistic studies indicate that the reaction is initiated through formation of a visible light-absorbing halogen bonding complex between the hydroquinone catalyst and the perfluoroalkyl halide radical precursor.

Diethylzinc-Mediated Radical 1,2-Addition of Alkenes and Alkynes

A novel diethylzinc-mediated radical 1,2-addition of perfluoroalkyl iodides to unactivated alkenes and alkynes is presented, which demonstrates a novel way to generate an ethyl difluoroacetate radical. This method is highly efficient and gives full conversions of the substrates, high yields of the products, and negligible byproducts and requires no column chromatography purifications. The mild conditions enable this protocol to exhibit excellent functional group compatibility.

A general and green fluoroalkylation reaction promoted: Via noncovalent interactions between acetone and fluoroalkyl iodides

The first example of visible light promoted fluoroalkylation reactions initiated via noncovalent interactions between acetone and fluoroalkyl iodides is presented. The reaction system features synthetic simplicity, mild reaction conditions without any photoredox catalyst, and high functional group tolerance. A wide range of substrate scopes such as alkenes, alkynes and (hetero)arenes were all compatible with the reaction system.

Metal-Free Activation of C-I Bonds and Perfluoroalkylation of Alkenes with Visible Light Using Phosphine Catalysts

An efficient metal-free, photomediated iodo perfluoroalkylation under mild conditions was developed. Using catalytic amounts (10 mol %) of phosphines and blue light irradiation, various olefins are transformed into the corresponding addition products with

Perfluoroalkylation of Alkenes by Frustrated Lewis Pairs

The activation of perfluoroalkyl iodides by the frustrated Lewis pair tris(pentafluorophenyl)borane and tri-tert-butylphosphine is described. By abstraction of both a fluorine and an iodine atom, an iodophosphonium fluoroborate salt is formed. In the presence of alkenes the corresponding iodoperfluoroalkylation products are generated regioselectively. First mechanistic investigations support a radical mechanism.

A NEW TIN(II) CHLORIDE-SILVER(I) ACETATE OR -LEAD(II) BROMIDE REAGENT FOR THE ADDITION OF F-ALKYL IODIDES TO ALKENES

A tin(II) chloride-silver(I) acetate or tin(II) chloride-lead(II) bromide reagent can efficiently promote the addition of F-alkyl iodides to various alkenes in anhydrous methanol at room temperature to afford the corresponding F-alkylated iodides in fairl