98369-78-9

Upstream product

• 100-42-5 styrene 
• 33756-42-2 tri-p-fluorophenylstibine 
• 1657-46-1 cis-4-fluorostilbene 
• 371-40-4 4-fluoroaniline 
• 459-45-0 4-fluorobenzenediazonium tetrafluoroborate 
• 459-04-1 4-Fluorophenylacetyl chloride 
• 405-50-5 p-Fluorophenylacetic acid 
• 1416889-59-2 1-(dimethyl(phenyl)silyl)-2-(4-fluorophenyl)ethanone 
• 18511-62-1 4-fluorostyrene oxide 
• 98-80-6 phenylboronic acid 
• 100-52-7 benzaldehyde 
• 352-11-4 1-chloromethyl-4-fluorobenzene 
• 7116-50-9 1-fluoro-4-methoxymethyl-benzene 
• 98369-94-9 1-Fluoro-4-methylselanylmethyl-benzene 

Downstream Products

• 1016896-29-9 (R)-1-acetoxy-1-phenyl-2-(4-fluorophenyl)ethane 
• 1422191-18-1 (S)-1-butyryloxy-1-phenyl-2-(4-fluorophenyl)ethane 

Relevant academic research and scientific papers

Heterogeneous visible-light-induced Meerwein hydration reaction of alkenes in water using mpg-C3N4 as a recyclable photocatalyst

A green and efficient visible light induced Meerwein hydration reaction of alkenes in aqueous medium using mpg-C3N4 as a recyclabe photocatalyst has been disclosed. This protocol provides a direct approach for the preparation of racemic alcohols via a free radical mechanism. Water acted as both a solvent and a reagent without any additives or co-solvents. The metal-free heterogeneous semiconductor is found to be fully recyclable at least 5 times without any significant reduction in activity. The Meerwein hydration reaction has an excellent substrate scope and gave the desired products in moderate to high yields. Furthermore, this reaction could be carried out under solar light irradiation and is applicable for large-scale reactions with satisfactory results.

Enantioselective 1,2-Anionotropic Rearrangement of Acylsilane through a Bisguanidinium Silicate Ion Pair

Highly enantioselective bisguanidinium-catalyzed tandem rearrangements of acylsilanes are reported. The acylsilanes were activated via an addition of fluoride on the silicon to form a penta-coordinate anionic silicate intermediate. The silicate then underwent alkyl or aryl group migration from the silicon atom to the neighboring carbonyl carbon atom (1,2-anionotropic rearrangement), followed by [1,2]-Brook rearrangement to provide the secondary alcohols in high yields with excellent enantioselectivities (up to 95% ee). The isolation of an α-silylcarbinol intermediate as well as DFT calculations revealed that the 1,2-anionotropic rearrangement occurred via a bisguanidinium silicate ion pair, which is the stereodetermining step. The chiral center formed is then retained without inversion through the subsequent [1,2]-Brook rearrangement. Crotyl acylsilanes were smoothly transformed into homoallylic linear crotyl alcohols with retention of E/Z geometry, and no branched alcohols were detected. This clearly suggested that the 1,2-anionotropic rearrangement occurred through a three-membered instead of a five-membered transition state.

Ni-catalysed regioselective 1,2-diarylation of unactivated olefins by stabilizing Heck intermediates as pyridylsilyl-coordinated transient metallacycles

We report a Ni-catalysed diarylation of unactivated olefins in dimethylpyridylvinylsilane by intercepting Heck C(sp3)-NiX intermediates, derived from aryl halides, with arylzinc reagents. This approach utilizes a modifiable pyridylsilyl moiety as a coordinating group that plays a dual role of intercepting oxidative addition species to promote Heck carbometallation, and stabilizing the Heck C(sp3)-NiX intermediates as transient metallacycles to suppress β-hydride elimination, and facilitate transmetalation/reductive elimination. This method affords 1,2-diarylethylsilanes, which can be readily oxidized to 1,2-diarylethanols that occur as structural motifs in 3-aryl-3,4-dihydroisocoumarin and dihydrostilbenoid natural products.

Synthetic method for diaryl-substituted ethanol compound serving as medical intermediate

The invention relates to a synthetic method for a diaryl-substituted ethanol compound serving as a medical intermediate shown as a formula (III). The method comprises the following steps: reacting a compound shown as a formula (I) and a compound shown as a formula (II) in a hermetic way in an organic solvent in the presence of a catalyst and an alkali; performing posttreatment at the end of the reaction to obtain a compound shown as the formula (III), wherein R1 and R2 are independently selected from H, alkyl with 1-6 carbon atoms, alkoxy with 1-6 carbon atoms or halogen; or R2 and a benzene ring which is connected with the R2 form a naphthalene ring. According to the synthetic method, the diaryl-substituted ethanol compound can be obtained at a high yield through comprehensive selection and coordination of a specific reaction substrate, the catalyst, the alkali and the organic solvent, and has good application prospect and industrial production potential in the field of synthesis of medical intermediates.

Nickel-catalyzed cross-coupling of styrenyl epoxides with boronic acids

Let's get multicatalytic! A Ni0 catalyst complexed with a biaryldialkyl monophosphine ligand facilitates C-C bond formation between styrenyl epoxides and aryl boronic acids (see scheme). X-ray analysis of a catalytically active nickel/ligand complex supports a redox pathway involving C sp 3-O bond activation. A variety of α-substituted alcohols were generated with good reaction efficiency by a multicatalytic sequence. Copyright

Regioselectivity of the rhodium-catalyzed hydroboration of vinyl arenes: Electronic twists and mechanistic shifts

Any substituent does it: The hydroboration of vinyl arenes with pinacol borane (HBPin) and cationic rhodium complexes selectively placed the boron proximal to the aryl rather than phenyl ring, regardless of whether this ring bears electron-donating or electron-withdrawing substituents. In competition experiments between styrene and various vinyl arenes, preferential hydroboration also occured at the substituted arene (see scheme). Hammett plots indicate a break in the mechanism. (Chemical Equation Presented).

Direct preparation of benzylic manganese reagents from benzyl halides, sulfonates, and phosphates and their reactions: Applications in organic synthesis

The use of highly active manganese (Mn)*, prepared by the Rieke method, was investigated for the direct preparation of benzylic manganese reagents. The oxidative addition of the highly active manganese to benzylic halides was easily completed under mild conditions. Moreover, benzylic manganese sulfonates and phosphates were prepared by direct oxidative addition of Mn* to the carbon-oxygen bonds of benzylic sulfonates and phosphates. The resulting benzylic manganese reagents were found to undergo cross-coupling reactions with a variety of electrophiles. Most of these reactions were carried out in the absence of any transition metal catalyst under mild conditions. In addition, the use of highly active manganese was also studied for preparation of homo-coupled products of functionalized benzyl halides without transition metal catalysts. These useful approaches provided not only a facile synthetic route to the preparation of resoricinolic lipids but a facile synthesis of functionalized 4-benzylpyridines by regioselective and chemo selective γ-addition of benzylic group to N-alkoxycarbonylpyridinum salts.

Silver catalyzed zinc Barbier reaction of benzylic halides in water

Benzylic chlorides react in aqueous dibasic potassium phosphate under silver catalysis with aromatic aldehydes in the presence of zinc dust to give 1,2-diaryl alcohols in moderate to good yields. Dimerization to bibenzyls and reduction of the halide are important side reactions. A wide range of substituted aromatic and heteroaromatic aldehydes and of substituted benzylic chlorides can be used. Aliphatic aldehydes and ketones are unreactive. A mechanism of two SET on the metal surface is discussed.

Photochemically induced coupling reaction of triarylstibines with olefins

Photoreaction of triarylstibines with styrenes resulted in the formation of 2-aryl-1-phenylethanols accompanied by air oxidation. Formation of the products has been explained by the valence expansion of the oxygen-antimony- styrene complex to a five-valent intermediate, followed by reductive coupling.

Reductive lithiation of arylalkyl methyl ethers

We have investigated the reductive cleavage of arylalkyl methyl ethers with an excess of lithium metal and a catalytic amount of naphthalene. The reaction proceeds regioselectively in the presence of various substituents on the aromatic ring, allowing access to a wide array of arylalkyl lithium derivatives some of which are not easily accessible by conventional methods.