116703-73-2

Upstream product

• 3446-89-7 4-(Methylthio)benzaldehyde 
• 122243-33-8 2,2,2-trifluoro-1-(4-methylsulfanyl-phenyl)-ethanone 
• 122035-81-8 2,2,2-trifluoro-1-(4'-methylsulfanylphenyl)ethanol 

Downstream Products

• 116703-76-5 N-(Methoxyethyl)-1-(4-(thiomethyl)phenyl)-2,2,2-trifluoroethylamine 
• 122425-19-8 N,N-Dimethyl-1-((4-dimethylamino)phenyl)-2,2,2-trifluoroethylamine 
• 122035-81-8 2,2,2-trifluoro-1-(4'-methylsulfanylphenyl)ethanol 
• 122035-83-0 (4-(2,2,2-trifluoroethyl)phenyl)(methyl)sulfane 

Relevant academic research and scientific papers

Photoredox-Catalyzed Ring-Opening Addition Reaction between Benzyl Bromides and Cyclic Ethers

A novel nucleophilic reaction between cyclic ethers and benzyl bromides is achieved under photoredox catalysis. The reaction proceeds through a single-electron-transfer (SET) pathway rather than a common SN2 mechanism. By two steps of reduction and oxidation, a benzyl bromide heterolyzes to give a carbocation and bromide ion under mild conditions, and then a cyclic ether captures both the carbocation and bromide ion to afford the addition product.

Generation of Carbocations under Photoredox Catalysis: Electrophilic Aromatic Substitution with 1-Fluoroalkylbenzyl Bromides

A novel Friedel-Crafts-type alkylation of arenes to access valuable 1-fluoroalkyl-1,1-biaryl compounds is established under mild conditions. The key to success is the efficient generation of a destabilized benzylic carbocation intermediate via two consecutive single-electron transfer processes by virtue of visible-light photoredox catalysis. This unique activation pattern avoids using strong Lewis acids and high temperatures that are required for generation of destabilized carbocations in traditional Friedel-Crafts reactions. This protocol demonstrates the first example of photoredox-catalyzed heterolysis of electronically deactivated benzylic C-Br bonds for the formation of destabilized carbocation intermediates.

The Extraordinarily Long Lifetimes and Other Properties of Highly Destabilized Ring-Substituted 1-Phenyl-2,2,2-trifluoroethyl Carbocations

A large bromide common ion rate depression is observed for the reactions of 1-(4-methoxyphenyl)- and 1-(4-(methylthio)phenyl)-2,2,2-trifluoroethyl bromides in largely aqueous solutions when the ionic strenght is maintained with weakly nucleophilic NaClO4