69843-10-3

Upstream product

• 1514-82-5 2-bromo-3,3,3-trifluoropropene 
• 873-77-8 (4-chlorphenyl)magnesium bromide 
• 321-37-9 4'-chloro-2,2,2-trifluoroacetophenone 
• 124-63-0 methanesulfonyl chloride 
• 1679-18-1 4-Chlorophenylboronic acid 
• 2065-66-9 methyl-triphenylphosphonium iodide 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 76953-98-5 1-(4-chlorophenyl)-1-(trifluoromethyl)ethanol 

Downstream Products

• 76953-98-5 1-(4-chlorophenyl)-1-(trifluoromethyl)ethanol 
• 69843-08-9 1-methoxy-4-(3,3,3-trifluoroprop-1-en-2-yl)benzene 
• 143264-63-5 1-chloro-4-(1,1-difluorohex-1-en-2-yl)benzene 

Relevant academic research and scientific papers

Electroreductive Cross-Coupling of Trifluoromethyl Alkenes and Redox Active Esters for the Synthesis of Gem-Difluoroalkenes

An electroreductive access to gem-difluoroalkenes has been developed through the decarboxylative/defluorinative coupling of N-hydroxyphtalimides esters and α-trifluoromethyl alkenes. The electrolysis is performed under very simple reaction conditions in a

Photoredox/Hydrogen Atom Transfer Cocatalyzed C-H Difluoroallylation of Amides, Ethers, and Alkyl Aldehydes

Herein, we report a method that combines hydrogen atom transfer and photoredox catalysis to achieve the dehydrogenative difluoroallylation of amides, ethers, and alkyl aldehydes. This operationally convenient method transforms a broad scope of substrates into the corresponding gem-difluoroalkenes via the construction of C(sp3)-C(sp3) or C(sp3)-C(sp2) bonds. Excellent functional group compatibility and high selectivity make this method have a wide range of substrate types and render it suitable for late-stage modification of pharmaceutical intermediates.

Photoredox relay-catalyzedgem-difluoroallylation of alkyl iodides

Herein, a new example of relay catalysis, using a combination of Mn2(CO)10and an iridium-based photocatalyst, is reported. In our relay catalytic reaction, the Mn catalyst and iridium-based photocatalyst catalyze the reaction at different stages in the desired sequence under the same reaction conditions, and do not inhibit each other. This convenient method transforms a broad scope of alkyl iodides into the correspondinggem-difluoroalkenesviaC(sp3)-C(sp3) bond construction. The protocol has good functional group tolerance and is suitable for the late-stage modification of multifunctional complex molecules.

Visible-Light-Driven Sulfonation of α-Trifluoromethylstyrenes: Access to Densely Functionalized CF3-Substituted Tertiary Alcohol

Reported herein is a visible-light-induced sulfonation of α-trifluoromethylstyrenes with sodium sulfinates, which provides a series of α-trifluoromethyl-β-sulfonyl tertiary alcohols. This new synthetic protocol is enabled by a charge-transfer complex between oxygen and sulfinates, featuring broad substrate scope and scalability. Excellent functional group compatibility and chemoselectivity render this method suitable for sulfonation of pharmaceutically relevant molecules. In the presence of D2O, deuteriotrifluorinated products were also obtained, further demonstrating the flexibility and synthetic potentials of this strategy.

Electrochemical heterodifunctionalization of α-CF3alkenes to access α-trifluoromethyl-β-sulfonyl tertiary alcohols

An unprecedented electrochemical heterodifunctionalization of α-CF3alkenes with benzenesulfonyl hydrazides was accomplished in this work, wherein a β-sulfonyl and a α-hydroxyl group were simultaneously incorporated across the olefinic double bond in a single operation. Consequently, a series of potentially medicinally valuable and densely functionalized α-trifluoromethyl-β-sulfonyl tertiary alcohols were assembled under mild conditions. Electrochemically-driven oxidative 1,2-difunctionlization of electron-deficient alkenes well obviates the need for oxidizing reagents, thus rendering this protocol more eco-friendly.

One-pot synthesis of α-trifluoromethylstyrenes from aryl ketones and the Ruppert–Prakash reagent

A new synthesis of α-trifluoromethylstyrenes from aromatic ketones and (trifluoromethyl) trimethylsilane is described. The reaction involves nucleophilic trifluoromethylation and elimination of trimethylsilanol, which are performed within one reaction fla

A Chiral Pentafluorinated Isopropyl Group via Iodine(I)/(III) Catalysis

An I(I)/(III) catalysis strategy to construct an enantioenriched fluorinated isostere of the iPr group is reported. The difluorination of readily accessible α-CF3-styrenes is enabled by the in situ generation of a chiral ArIF2 species to forge a stereocentre with the substituents F, CH2F and CF3 (up to 95 %, >20:1 vicinal:geminal difluorination). The replacement of the metabolically labile benzylic proton results in a highly preorganised scaffold as was determined by X-ray crystallography (π→σ* and stereoelectronic gauche σ→σ* interactions). A process of catalyst editing is disclosed in which preliminary validation of enantioselectivity is placed on a structural foundation.

Visible-Light-Induced Deoxygenation/Defluorination Protocol for Synthesis of γ,γ-Difluoroallylic Ketones

Herein, we describe an efficient, practical photocatalytic deoxygenation/defluorination protocol for the synthesis of γ,γ-difluoroallylic ketones from commercially available aromatic carboxylic acids, triphenylphosphine, and α-trifluoromethyl alkenes. The protocol has good functional group tolerance and a broad substrate scope. Using this method, we accomplished the late-stage functionalization of several bioactive molecules.

Photoinduced Single-Electron Transfer as an Enabling Principle in the Radical Borylation of Alkenes with NHC–Borane

A photoinduced SET process enables the direct B?H bond activation of NHC–boranes. In contrast to common hydrogen atom transfer (HAT) strategies, this photoinduced reaction simply takes advantage of the beneficial redox potentials of NHC–boranes, thus obviating the need for extra radical initiators. The resulting NHC–boryl radical was used for the borylation of a wide range of α-trifluoromethylalkenes and alkenes with diverse electronic and structural features, providing facile access to highly functionalized borylated molecules. Labeling and photoquenching experiments provide insight into the mechanism of this photoinduced SET pathway.

Visible-Light-Induced Radical Defluoroborylation of Trifluoromethyl Alkenes: An Access to gem-Difluoroallylboranes

A photoredox-catalyzed defluoroborylation of trifluoromethyl alkenes with N-heterocyclic carbene boranes is described for the synthesis of gem-difluoroallylboranes. This protocol exhibits a broad substrate scope and good functional group compatibility, which enables the late-stage functionalization of structurally complex compounds. Further transformations of the defluoroborylation products to valuable CF2-containing molecules are also demonstrated. (Figure presented.).