36029-60-4

Upstream product

• 696-62-8 para-iodoanisole 
• 219951-10-7 3,3,3-trifluoro-1,2-diphenyl-1-phenylsulfonylpropene 
• 867182-59-0 (Z)-3,3,3-trifluoro-2-iodo-1-(4-methoxyphenyl)-1-phenylpropene 
• 98-80-6 phenylboronic acid 
• 591-50-4 iodobenzene 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 219951-09-4 β-CF3-α,β-diphenylvinyl sulfide 
• 1233-23-4 (E)-1-(4-methoxyphenyl)-1,2-diphenylethylene 
• 72474-39-6 4-(1,2-diphenylvinyl)anisole 
• 1417821-09-0 C₂₂H₁₉F₃O₂ 
• 108-86-1 bromobenzene 
• 1003322-00-6 (Z)-3,3,3-trifluoro-1-(4-methoxyphenyl)-1-phenyl-2-tosyloxypropene 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 154669-95-1 3,3,3-trifluoro-1,2-diphenylpropan-1-one 

Downstream Products

• 52033-69-9 3-(4-methoxyphenyl)-2-phenyl-1H-indene 
• 53347-55-0 6-methoxy-2,3-diphenyl-1H-indene 
• 77599-17-8 (E)-3,3,3-trifluoro-1-{4-[2-(2-hydroxyethylamino)ethoxy]phenyl}-1,2-diphenylpropene 

Relevant academic research and scientific papers

Sunlight-driven trifluoromethylation of olefinic substrates by photoredox catalysis: A green organic process

The principles and utility of photoredox catalysis in organic synthesis are described. After a brief description of the features of the two types of catalytic photoredox processes following the reductive quenching cycle (RQC) and the oxidative quenching cycle (OQC), the discussion is focused on organic transformations based on OQC, in particular the trifluoromethylation of olefinic substrates with electrophilic trifluoromethylating reagents furnishing solvolytic addition products and substitution products. It is concluded that catalytic photoredox systems are green from the point of view of harmfulness, safety, and energy source (visible light, including sunlight). Future prospects of photoredox catalysis will be also discussed.

Direct C-H trifluoromethylation of di- and trisubstituted alkenes by photoredox catalysis

Background: Trifluoromethylated alkene scaffolds are known as useful structural motifs in pharmaceuticals and agrochemicals as well as functional organic materials. But reported synthetic methods usually require multiple synthetic steps and/or exhibit lim

Three-component oxytrifluoromethylation of alkenes: Highly efficient and regioselective difunctionalization of C=C bonds mediated by photoredox catalysts

Here comes the sun: A facile vicinal difunctionalization of alkenes, oxytrifluoromethylation, was established by visible-light-driven photoredox catalysis. Judicious choice of the CF3 source is key. Nucleophiles such as water, alcohols, and carboxylic acids can be used in this highly efficient (2-4 h) and regioselective (100 %) transformation using light-emitting diode (LED) lamps and natural sunlight. SET=single-electron transfer. Copyright

Niobium-catalyzed activation of CF3 group on alkene: Synthesis of substituted indenes

A CF3 group attached to an alkene functionality was activated by a zero-valent niobium catalyst to generate niobium alkenylcarbenoid species. The niobium carbenoid species then underwent insertion to an internal aromatic C-H σ bond to give inde

Straightforward synthesis of CF3-substituted triarylethenes by stereoselective threefold cross-coupling reactions

Any way round: The palladium-catalyzed threefold cross-coupling reaction of 1,1-dibromo-3,3,3-trifluoro-2-tosyloxypropene with aryl boronic acids provides a versatile route to CF3-substituted triarylethenes (see scheme). The CF3 group is essential for the high Z selectivity in the first coupling reaction, which is the key step in the process. Any of the ethene stereoisomers can be prepared simply by changing the order of the aryl boronic acids. (Chemical Equation Presented).

Highly regio- and stereo-selective carbometallation reaction of fluorine-containing internal acetylenes with organocopper reagents

The carbometallation reactions of fluoroalkylated internal alkynes with various organocopper reagents derived from organolithium, Grignard, and organozinc reagents were examined. All carbocupration reactions proceeded smoothly in a highly regio- and stereo-selective manner to give the corresponding vinylcopper intermediates. The intermediates reacted with H + smoothly, leading to the trisubstituted alkenes in high to excellent yields, whereas they reacted only with strictly limited carbon electrophiles such as allyl-, crotyl-, methallyl bromide, etc, probably due to the low reactivity exerted by an electron-withdrawing fluoroalkyl group. Treatment of vinylcopper with iodine resulted in a high yield of the corresponding vinyl iodide, which was employed successfully for Suzuki-Miyaura and Sonogashira cross-coupling reactions. In addition, two key reactions, the carbocupration and the Suzuki-Miyaura cross-coupling reaction realized the first highly stereoselective total synthesis of anti-estrogen drug, panomifene.

A highly stereoselective preparation of CF3-substituted 1-aryl-1,2-diphenylethenes: Application to the synthesis of panomifene

β-CF3-α,β-diphenylvinyl sulfide 3a was prepared stereoselectively in 77% yield from the reaction of 2 with phenyllithium at room temperature for 5 h. Oxidation of 3a with MCPBA afforded the corresponding vinyl sulfone 4a, in which (E)-4a can be

A highly regio- and stereoselective carbocupration of fluoroalkylated internal alkynes: A short total synthesis of the antiestrogenic drug panomifene

(Equation presented) A highly regio- and stereoselective carbometalation reaction of fluoroalkylated internal alkynes with organocopper reagents is described. This reaction is utilized successfully in the short, stereoselective total synthesis of the antiestrogenic drug panomifene.

A facile stereocontrolled approach to CF3-substituted triarylethenes: Synthesis of panomifene

The stereoselective preparation and Pd-catalyzed cross-coupling reaction of boronates 2 provides a new general and convenient route to CF 3-substituted triaryl ethenes 3, in which the CF3 and Ar3 groups are cis to each other. The synthetic potential was demonstrated by the total synthesis of panomifene (Ar1 = Ar 3 = Ph, Ar2 = 4-(OHCH2CH2NHCH 2CH2O)-C6H4). Bpin = (pinacolato)boryl.

Preparation of α- or β-trifluoromethylated vinylstannanes and their cross-coupling reactions

α - or β-Trifluoromethylated vinylstannanes 1, 2a, 3 and 4 were prepared form 1,1-bis(phenylthio)-2,2,3,3,3-pentafluoropropylbenzene (5) via several steps. The cross-coupling arylation reactions of 1-4 with aryl iodides bearing a bromo, methoxy, methyl, n