82575-21-1

Upstream product

• 677-21-4 1,1,1-trifluoropropylene 
• 588-72-7 [(E)-2-bromoethenyl]benzene 
• 138024-29-0 (E)-1,1-Difluoro-5-phenyl-penta-1,4-dien-3-ol 
• 14371-10-9 (E)-3-phenylpropenal 
• 28010-12-0 5-phenylpenta-2,4-dienoic acid 
• 100-42-5 styrene 
• 381-98-6 trifluoromethyacrylic acid 
• 371-67-5 2,2,2-trifluorodiazoethane 
• 104-55-2 3-phenyl-propenal 
• 887144-94-7 Togni's reagent II 
• 16939-57-4 (E)-buta-1,3-dienylbenzene 
• 2314-97-8 iodotrifluoromethane 
• 185152-35-6 (4E)-5-phenylpenta-2,4-dienoic acid 
• 1226574-99-7 (E)-diphenyl-β-(trifluoromethyl)vinylsulfonium trifluoromethanesulfonate 

Downstream Products

• 144434-31-1 4-phenyl-7-trifluoromethyl-3a,4,7,7a-tetrahydroisobenzofuran-1,3-dione 
• 144434-37-7 ethyl t-2-phenyl-t-5-(trifluoromethyl)-3-cyclohexene-r-1-carboxylate 
• 144434-37-7 ethyl c-2-phenyl-c-5-(trifluoromethyl)-3-cyclohexene-r-1-carboxylate 

Relevant academic research and scientific papers

Rhodium(III)-catalyzed β-arylation and- alkenylation of α-trifluoromethylacrylic acid

The β-arylation and - alkenylation of trifluoromethylacrylic acid with arylboronic acids and alkenes proceed smoothly under rhodium(III) catalysis. The procedures provide useful synthetic routes from readily available building brocks to β-aryl-α-trifluoromethylpropanoic acid and 5, 5, 5-trifluoro-1, 3-butadiene derivatives. Some of the obtained butadienes exhibit strong fluorescence in the solid state.

Iron(III) Porphyrin Catalyzed Olefination of Aldehydes with 2,2,2-Trifluorodiazoethane (CF3CHN2)

An efficient method for the iron(III) porphyrin catalyzed olefination of various aldehydes with 2,2,2-trifluorodiazoethane under neutral conditions is described. This transformation was shown to have a broad substrate scope and provide the corresponding CF3-substituted alkenes in good yields. The number of equivalents of PPh3 that is used in this reaction is crucial to the success of the olefination process. This reaction is a useful supplement to the synthetic applications of CF3CHN2.

Facile synthesis of 1-trifluoromethylalkenes via the decarboxylation of α-trifluoromethyl-β-lactones

DCC-mediated cyclodehydration of α-trifluoromethyl-β-hydroxy acids provides α-trifluoromethylated β-lactone intermediates, without loss of stereoselectivity. These lactones undergo facile decarboxylation providing a simple route to obtain both alkyl and aryl trifluoromethylated alkenes in excellent yields and stereoselectivity.

A general synthesis of fluoroalkylated alkenes by palladium-catalyzed Heck-type reaction of fluoroalkyl bromides

An efficient palladium-catalyzed Heck-type reaction of fluoroalkyl halides, including perfluoroalkyl bromides, trifluoromethyl iodides, and difluoroalkyl bromides, has been developed. The reaction proceeds under mild reaction conditions with high efficiency and broad substrate scope, and provides a general and straightforward access to fluoroalkylated alkenes which are of interest in life and material sciences.

Oxy-trifluoromethylation of alkenes and its application to the synthesis of β-trifluoromethylstyrene derivatives

Oxy-trifluoromethylation of di-substituted styrenes and dienes was achieved by using Cu/Togni's reagent system. Not only gem-di-substituted styrenes, but also a β-methylstyrene derivative were transformed to the corresponding oxy-trifluoromethylation prod

Room temperature decarboxylative trifluoromethylation of α,β-unsaturated carboxylic acids by photoredox catalysis

A visible-light-induced decarboxylative trifluoromethylation of α,β-unsaturated carboxylic acids, which uses the Togni reagent as the CF3 source is disclosed. The corresponding trifluoromethylated alkenes were obtained in moderate to high yields with excellent functional group tolerance at ambient temperature. Preliminary mechanistic analyses suggest a radical-type mechanism. The Royal Society of Chemistry 2014.

Copper-and iron-catalyzed decarboxylative tri-and difluoromethylation of α,β-unsaturated carboxylic acids with CF3SO2Na and (CF2HSO2)2Zn via a radical process

A copper-catalyzed decarboxylative trifluoromethylation of various α,β-unsaturated carboxylic acids by using a stable and inexpensive solid, sodium trifluoromethanesulfinate (CF3SO2Na, Langlois reagent), was developed. In addition, an iron-catalyzed difluoromethylation of aryl-substituted acrylic acids by using zinc difluoromethanesulfinate (DFMS, (CF2HSO2)2Zn, Baran reagent) via a similar radical process was also achieved.

Highly selective activation of vinyl C-S bonds over aryl C-S bonds in the Pd-catalyzed coupling of (E)-(β-trifluoromethyl)vinyldiphenylsulfonium salts: Preparation of trifluoromethylated alkenes and dienes

We describe the Suzuki coupling reaction of (E)-(β-trifluoromethyl) vinyldiphenylsulfonium salts with arylboronic acid. The highly efficient and selective reaction provides a useful and mild method for the synthesis of trifluoromethylated alkenes and dienes. Subsequent DFT studies showed that the oxidative addition transition state of the vinyl C-S bond is much more favorable (11.7 kcal mol-1) than that of the aryl C-S bond. Copyright

Iron(II)-catalyzed trifluoromethylation of potassium vinyltrifluoroborates

Exchanging BF3 by CF3: The title reaction proceeds under exceedingly mild reaction conditions and provides 2-arylvinyl- and 2-heteroarylvinyl-substituted substrates with E/Z selectivities of more than 95:5. Experimental observations suggest that the reaction does not proceed through a transmetalation of the RBF3K species to the iron catalyst. Copyright

Sodium dithionite initiated addition of 1-bromo-1-chloro-2,2,2-trifluoroethane to allylaromatics. Facile synthesis of conjugated dienes substituted with terminal CF3 group

Sodium dithionite effectively promotes the addition of 1-bromo-1-chloro-2,2,2-trifluoroethane to the terminal double bond of allylbenzenes 1. The reactions proceeded in MeCN/H2O to give a 3:1 mole ratio of diastereoisomers of 1-(2-bromo-4-chloro-5,5,5-trifluoropentyl)benzenes 2 as the main products together with small amounts of its reductive debromination products 3. Total yields of 2 and 3 were dependent on the nature of the aromatic ring substituents in 1. Treatment of adducts 2 with DBU in refluxing hexanes resulted in double dehydrohalogenation affording, in good yields, conjugated dienes 4 (1,1,1-trifluoro-5-phenyl-2,4-pentadienes) terminated with the CF3 group at the one end and the phenyl group at the opposite end. These dienes were found to be sufficiently reactive to undergo Diels-Alder condensation with active dienophiles to give trifluoromethylated carbocycles. The reactions of CF3CHClBr with allylheterocycles were less successful and lead to low yields of mixtures of hardly separable compounds or to polymeric resins.