339-23-1

Upstream product

• 403-42-9 1-(4-fluorophenyl)ethanone 
• 917-54-4 methyllithium 
• 345-83-5 4-fluorobenzophenone 
• 403-41-8 1-(4-Fluorophenyl)ethanol 
• 5123-13-7 5,5-dimethyl-2-phenyl-1,3,2-dioxaborinane 
• 98-80-6 phenylboronic acid 
• 98-86-2 acetophenone 
• 352-34-1 4-fluoro-1-iodobenzene 
• 460-00-4 1-Bromo-4-fluorobenzene 
• 143-66-8 sodium tetraphenyl borate 
• 352-13-6 4-flourophenylmagnesium bromide 

Downstream Products

• 128270-94-0 2-(4'-nitrophenyl)-3-ethyl-2,3-bis(4''-fluorophenyl)pentane 
• 128270-92-8 2-(4'-fluorophenyl)-2-(4''-nitrophenyl)-3-ethyl-3-<4'''-(trifluoromethyl)phenyl>pentane 
• 395-21-1 1-(4-fluorophenyl)-1-phenylethylene 
• 345-83-5 4-fluorobenzophenone 

Relevant academic research and scientific papers

Preparation of Functionalized Diaryl- and Diheteroaryllanthanum Reagents by Fast Halogen–Lanthanum Exchange

Aryl and heteroaryl halides (X=Br, I) undergo a fast and convenient halogen–lanthanum exchange with nBu2LaMe, which leads to functionalized diaryl- and diheteroaryllanthanum derivatives. Subsequent trapping reactions with selected electrophiles, such as ketones, aldehydes, or amides, proceeded smoothly at ?50 °C in THF, affording polyfunctionalized alcohols and carbonyl derivatives. Kinetic competition experiments revealed a similar reactivity trend as for Br/Mg exchange, but 106-times higher rates, making it comparable to Br/Li exchange.

Scandium(III) Trifluoromethanesulfonate Catalyzed Selective Reactions of Donor–Acceptor Cyclopropanes with 1,1-Diphenylethanols: An Approach to Polysubstituted Olefins

An unexpected synthetic approach to polysubstituted olefins through the scandium(III) trifluoromethanesulfonate catalyzed ring-opening reaction of donor–acceptor cyclopropanes with 1,1-diphenylethanols was developed. The reactions, which are experimentally easy to handle, feature tolerance of various functional groups and mild reaction conditions. On the basis of experimental evidence, a plausible mechanism was also proposed.

Rhodium(I)-n-heterocyclic carbene-catalyzed addition of sodium tetraphenylborate to ketones to form tertiary alcohols

Rhodium complexes ([Rh(COD)(NHC)Cl]) were synthesized by the reaction of bis(1,3-dialkylperhydrobenzimidazolin-2-ylidene) with [RhClCOD]2 in toluene and characterized by elemental analysis, 1H NMR, 13C NMR and IR spectroscopy. These complexes were used as catalysts for the addition of sodium tetraphenylborate to aromatic ketones and corresponding tertiary alcohols were obtained in good yields.

Added-metal-free catalytic nucleophilic addition of Grignard reagents to ketones

On the basis of the investigation of the combinational effect of quaternary ammonium salts and organic bases, an added-metal-free catalytic system for nucleophilic addition reactions of a variety of Grignard reagents to diverse ketones in THF solvent has been developed to produce tertiary alcohols in good to excellent yields. By using tetrabutylammonium chloride (NBu4Cl) as a catalyst and diglyme (DGDE) as an additive, this system strongly enhances the efficiency of addition at the expense of enolization and reduction. NBu 4Cl should help to shift the Schlenk equilibrium of Grignard reagents to the side of dimeric Grignard reagents to favor the additions of Grignard reagents to ketones via a favored six-membered transition state to form the desired tertiary alcohols, and DGDE should increase the nucleophilic reactivities of Grignard reagents by coordination. This catalytic system has been applied in the efficient synthesis of Citalopram, an effective U.S. FDA-approved antidepressant, and a recyclable version of this catalytic synthesis has also been devised.

Controlled alcohol-carbonyl interconversion by nickel catalysis

All in one pot: A general synthetic platform allows the interconversion of alcohols and carbonyl compounds in a predictable and controlled fashion in one pot. Under the action of a Ni catalyst, PhCl, CsF, and arylboronates, several multistep alcohol-carbonyl interconversions have been achieved with good overall efficiency (see scheme). A one-pot nickel-catalyzed synthesis of flumecinol (a hepatic microsomal enzyme inducer) has also been demonstrated. Copyright

Zinc(ii)-catalyzed Grignard additions to ketones with RMgBr and RMgI

Highly efficient alkylations and arylations of ketones with Grignard reagents (RMgBr and RMgI) have been developed using catalytic ZnCl2, Me3SiCH2MgCl, and LiCl. Tertiary alcohols were obtained in high yields with high chemoselectivities, while minimizing undesired side products produced by reduction and enolization.

Zinc(II)-catalyzed addition of grignard reagents to ketones

(Figure presented) The addition of organometallic reagents to carbonyl compounds has become a versatile method for synthesizing tertiary and secondary alcohols via carbon-carbon bond formation. However, due to the lack of good nucleophilicity or the presence of strong basicity of organometallic reagents, the efficient synthesis of tertiary alcohols from ketones has been particularly difficult and, thus, limited. We recently developed highly efficient catalytic alkylation and arylation reactions to ketones with Grignard reagents (RMgX: R = alkyl, aryl; X = Cl, Br, I) using ZnCl2, Me3SiCH 2MgCl, and LiCl, which effectively minimize problematic side reactions. In principle, RMgBr and RMgI are less reactive than RMgCl for the addition to carbonyl compounds. Therefore, this novel method with homogeneous catalytic ZnCl2·Me3SiCH2MgCl·LiCl is quite attractive, since RMgBr and RMgI, which are easily prepared and/or commercially available, like RMgCl, can be applied successfully. As well as ketones and aldehydes, aldimines were effectively applied to this catalysis, and the corresponding secondary amines were obtained in high yield. With regard to mechanistic details concerning β-silyl effect and salt effect, in situ-prepared [R(Me3SiCH2)2Zn] -[Li]+[MgX2]m[LiCl]n (X = Cl/Br/I) is speculated to be a key catalytic reagent to promote the reaction effectively. The simplicity of this reliable ZnCl2·Me 3SiCH2MgCl·LiCl system in the addition of Grignard reagents to carbonyl compounds might be attractive for industrial as well as academic applications.

Gold(I)-catalyzed oxidative cleavage of a C-C double bond in water

Oxidative cleavage of the C=C bond to afford ketone or aldehyde products with tert-butyl hydrogenperoxide (TBHP) as the oxidant can be catalyzed by AuCl with neocuproine (1) in water.

Hammett ρ of reactions of MeLi with benzophenones

Relative rates of reactions of MeLi with benzophenones in diethyl ether at 0 °C that furnish methyldiaryl-methanols were determined using slow addition of a MeLi solution to solutions containing an excess of two benzophenones. The additions exhibit a Hammett p of 0.94.

Transition-State Polarization in Cleavage of C-C Bonds in Radical Anions

The substituent effect on the rate of C-C bond cleavage in radical anions of 1-(4-nitrophenyl)-2-(substituted-phenyl)-1,1,2,2-tetraethylethanes has been explored.The data provide evidence for two distinctive modes of bond scission.One mode is characterized by a significant negative charge transfer across the scissile bond in the transition state.Such polarization of the transition state is in contradiction to the prediction based on the fragments' stability.The second mode, dominant in cases where the charge shift leads to negative charge accumulation on an already electron-rich fragment, involves a ?* radical anion.Both modes point to a general kinetic preference for a cleavage of radical anions that allows for charge delocalization across the scissile bond.