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• 329-98-6 phenylmethylsulphonyl fluoride 
• 1100-88-5 benzyltriphenylphosphonium chloride 
• 960-16-7 tributylphenylstannane 
• 1023-17-2 4-methoxyphenyl benzyl ketone 
• 16721-45-2 triphenyl(phenylmethylene)phosphorane 
• 340-04-5 1-phenyl-2,2,2-trifluoromethylethanol 
• 1666-17-7 benzaldehyde p-toluenesulfonylhydrazone 
• 100-39-0 benzyl bromide 
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• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 40389-50-2 (1-bromoethene-1,2-diyl)dibenzene 
• 591-50-4 iodobenzene 

Relevant academic research and scientific papers

Syntheses, structures, and thermolyses of pentacoordinate 1,2-oxastibetanes: Potential intermediates in the reactions of stibonium ylides with carbonyl compounds

Pentacoordinate 1,2-oxastibetanes 14a-d, which are formal [2 + 2]-cycloadducts of the reactions of stibonium ylides with carbonyl compounds, were successfully synthesized by the reactions of the corresponding bromo-2-hydroxyalkylstiboraiies with NaH. The

Synthesis of hindered and functionalized 1-CF3 substituted olefins via a carbolithiation-elimination-metalation cascade

Addition of organolithium reagents to trifluoromethyl enol ethers 1a-d and thio enol ethers 2a provided stereoselectively the corresponding trisubstituted fluoroalkenes 3a-d in 70-90% yields. The products could themselves react with organolithium reagents and undergo a vinyl metalation providing, after trapping with an electrophile, tetrasubstituted olefins in excellent yields and with stereoselectivity. This method can be applied to other fluoroalkyl enol ethers (Rf = C2F5). The product, tetrasubstituted olefin, can be obtained directly from enol ether with 2 equiv of reagent through a carbolithiation-elimination-metalation cascade.

Z-trifluoromethyl thioenol ethers, enol ethers, and enamines; reactivity towards organolithium reagents

Trifluoromethyl enol ethers and thioenol ethers conjugated with an unsaturation in the β-position undergo addition/elimination reactions with organolithium reagents to yield the corresponding trifluoromethyl alkenes while preserving the geometry of the do

Highly regio- and stereoselective hydrometallation reactions of fluorine-containing internal alkynes: Novel approaches to fluoroalkylated alkenes

Hydroalumination, hydrocupration, and hydroboration reactions of various fluorine-containing alkynes were investigated. The alkyne reacted smoothly with 2.0 equiv. of Red-Al at -78°C to give the hydroaluminated adduct in a highly regio- and stereoselectiv

Synthesis of (Z)-α-Trifluoromethyl Alkenyl Triflate: A Scaffold for Diverse Trifluoromethylated Species

An efficient method for the synthesis of (Z)-selective α-trifluoromethyl alkenyl triflates is described. As an important fluorinated building block, it is utilized successfully for the synthesis of various trifluoromethyl derivatives such as diarylethylen

Wittig Reactions of Phosphonium Ylides Bearing the Phosphastibatriptycene Skeleton with Carbonyl Compounds

To investigate effects of the tridentate ligand on the reactivity of a 1,2-oxaphosphetane, an intermediate of the Wittig reaction, the reactions of phosphonium ylides 1 and 2 bearing the phosphastibatriptycene skeleton with carbonyl compounds have been conducted and compared with those of triphenyl phosphorus compounds. Non-stabilized and semi-stabilized phosphonium ylides 1 and 2 bearing the tridentate ligand were generated from the corresponding phosphonium salts 3 and 4, which were prepared by the reactions of a phosphastibatriptycene with ethyl iodide and benzyl bromide, respectively. The reactions of ylides 1 and 2 with benzaldehyde showed high E-selectivity, in sharp contrast to those of triphenylphosphonium ylides 5 and 6 giving Z-alkenes as a major product. However, the reaction of 1 with trifluoroacetophenone gave E/Z-alkenes 10 in the ratio of 69:31 together with phosphine oxide 13, which showed slightly higher selective E-alkene formation compared with the reaction of non-stabilized ylide 5 (E/Z ratio of 51:49). The results showed that the reactions did not proceed with high stereoselectivity as same as those of semi-stabilized phosphonium ylides 2 and 6. In the VT-31P{1H} NMR spectra of the reaction mixture of non-stabilized phosphonium ylide 1 with trifluoroacetophenone, the signals due to the corresponding 1,2-oxaphosphetanes were observed as multi signals in high field around -54 ppm at -80°C, which was different from the reaction of ylide 5 showing two signals.

Copper(i)-catalyzed wittig olefination reactions of N-tosylhydrazones with trifluoromethylketones

Cuprous iodide-catalyzed Wittig olefination reactions of N-tosylhydrazones with trifluoromethylketones are reported. This procedure provides an efficient method for the synthesis of various trifluoromethyl-substituted alkenes in moderate to good yields (up to 89 % yield) and good stereoselectivity (up to 93 % E-selectivity). To the best of our knowledge, it is the first report of a Wittig reaction of N-tosylhydrazones with ketones. Copyright

One-pot multistep synthesis of trisubstituted alkenes from N -tosylhydrazones and alcohols

A one-pot procedure for the synthesis of trisubstituted alkenes from N-tosylhydrazones and alcohols is reported. This procedure combines the aerobic oxidation reaction and Wittig reaction in one pot, which avoids using of environmentally toxic oxidants and isolation of the intermediates. The simple procedure makes it very attractive for the synthesis of trisubstituted alkenes when alcohols are used as starting materials. A variety of trisubstituted alkenes as well as trifluoromethyl-substituted alkenes were obtained in moderate to good yields (up to 84%) with good E-selectivity (up to 99%). Georg Thieme Verlag Stuttgart.New York.

Pd-carbene migratory insertion: Application to the synthesis of trifluoromethylated alkenes and dienes

Pd-catalyzed cross-coupling of halides with CF3-substituted diazo compounds or N-tosylhydrazones has been explored for the synthesis of CF3-substituted alkenes and 1,3-butadienes. Pd-carbene migratory insertion plays the key role in these transformations. Copyright

A convenient and mild chromatography-free method for the purification of the products of Wittig and Appel reactions

A mild method for the facile removal of phosphine oxide from the crude products of Wittig and Appel reactions is described. Work-up with oxalyl chloride to generate insoluble chlorophosphonium salt (CPS) yields phosphorus-free products for a wide variety of these reactions. The CPS product can be further converted into phosphine.