957770-94-4

Upstream product

• 100-52-7 benzaldehyde 
• 131379-14-1 4-cyanophenylzinc bromide 
• 105-07-7 4-cyanobenzaldehyde 
• 98-80-6 phenylboronic acid 
• 100-58-3 phenylmagnesium bromide 
• 623-00-7 4-bromobenzenecarbonitrile 

Relevant academic research and scientific papers

Application of a Heterogeneous Chiral Titanium Catalyst Derived from Silica-Supported 3-Aryl H8-BINOL to Enantioselective Alkylation and Arylation of Aldehydes

A 3-aryl H8-BINOL was grafted on the surface of silica gel using a hydrosilane derivative as a precursor, and the resulting silica-supported ligand (6 mol %) was employed in the enantioselective alkylation and arylation of aldehydes in the pres

Catalytic enantioselective arylation of aldehydes by using functionalized grignard reagents generated from aryl bromides

An efficient catalytic method has been developed for the enantioselective synthesis of functionalized diarylmethanols starting from aryl bromides and aldehydes. In the presence of (R)-3-(3,5-diphenylphenyl)BINOL (2 mol%) and titanium tetraisopropoxide, fu

Catalytic enantioselective alkylation and arylation of aldehydes by using grignard reagents

We have developed an efficient and practical method for the catalytic enantioselective alkylation and arylation of aldehydes by using Grignard reagents in combination with titanium tetraisopropoxide. Grignard reagents and titanium tetraisopropoxide are mixed in a molar ratio of ca. 1:2. In the presence of catalyst (24mol%), which is formed in situ from a BINOL ligand 4a and 4b and titanium tetraisopropoxide, the resulting mixed titanium reagents undergo addition to aldehydes with high enantioselectivities (typically >90% ee) and high yields. The method is applicable to various combination of aldehydes (R1CHO; R1 = aryl, heteroaryl, 1-alkenyl, and alkyl) and Grignard reagents (R2MgX; R2 = primary alkyl and aryl). Thus, a variety of enantiomerically enriched secondary alcohols (R1CH*(OH)R2) can be prepared. It has also been demonstrated that functionalized aryl Grignard reagents can be employed to generate highly functionalized diarylmethanols. The preparative utility of the method has been shown by the fact that the reaction is operationally simple, can be carried out on a 10-mmol scale without any difficulty, and the ligands can be readily recovered.

On the scope of trimethylaluminium-promoted 1,2-additions of ArZnX reagents to aldehydes

A practical asymmetric 1, 2 addition of functionalised arylzinc hal ides to aromatic and aliphatic aldehydes is described by the use of amino alcohol catalysis in the presence of AlMe3. The process is simple to carry out, uses only commercially available reagents/ligands and provides moderate to good (80-96% ee) enantioselectivities for a wide range of substrates. Either commercial ArZnX reagents or those prepared in situ from low cost aryl bromides can be used. In the latter case electrophilic functional groups are tolerated (CO2Et, CN). The reaction relies on rapid exchange between ArZnX and AlMe3 to generate mixed organometallic species that lead to the formation of a key intermediate that is distinctly different from the classic "anti" transition states of Noyori. NMR monitoring and related experments have been used to probe the validity of the proposed selective transition state.

Catalytic enantioselective synthesis of diarylmethanols from Aryl bromides and aldehydes by using organolithium reagents

A general method has been developed for preparing enantioenriched secondary alcohols by starting from aryl bromides and aldehydes. Aryl bromides were first treated with BuLi, and the resulting aryllithium reagents were mixed with titanium tetraisopropoxide and magnesium bromide. The reaction of aldehydes with the resulting mixed titanium reagents, in the presence of 3-(3,5- diphenylphenyl)-H8-BINOL (2 mol-%) and titanium tetraisopropoxide, furnished the corresponding alcohols in high enantioselectivities and in high yields. Copyright

Addition reaction of arylboronic acids to aldehydes and α,β-unsaturated carbonyl compounds catalyzed by conventional palladium complexes in the presence of chloroform

Arylboronic acids react with aldehydes and α,β-unsaturated carbonyl compounds in the presence of a base and a catalytic amount of a palladium(0) complex with chloroform, affording the corresponding addition products in good yields, and chiral benzhydrol was obtained with up to 43% e.e. using (S,S)-bppm as a ligand. General palladium complexes have no catalytic activity without chloroform. Because chloroform is essential for this reaction, these reactions would be promoted by dichloromethylpalladium(II) species.

Asymmetric 1,4-addition of organoboronic acids to α,β-unsaturated ketones and 1,2-addition to aldehydes catalyzed by a palladium complex with a ferrocene-based phosphine ligand

A combination of palladium with ferrocene-based phosphine ligand with a carbon-bromine bond was found to be a good catalyst for the 1,4-addition of arylboronic acids to α,β-unsaturated ketones and the 1,2-addition to aldehydes. Using Pd(dba)2 and (S,Rp)-[1-(2-bromoferrocenyl)ethyl]diphenylphosphine (S,Rp)-1, 3-phenylcyclohexanone was obtained from the reaction of 2-cyclohexen-1-one with phenylboronic acid in the presence of K2CO3 in toluene at room temperature after 3 h in 92% yield with 76% ee. In the 1,2-addition of 4-methylphenylboronic acid to benzaldehyde, 96% of (4-methylphenyl)phenylmethanol was afforded after 24 h, while the enantiomeric excess was only 6%.

Catalytic asymmetric aryl transfer reactions to aldehydes with grignard reagents as the aryl source

A study was conducted to demonstrate a practical and efficient method for asymmetric arylation of aldehydes, using aryl Grignard reagents in combination with titanium tetraisopropoxide. It was demonstrated that a variety of diarylmethanols can be obtained

Direct asymmetric catalytic 1,2-addition of RZnX to aldehydes promoted by AlMe3 and reversal of expected stereochemistry

Addition of AlMe3 to commercial THF solutions of RZnX (R = aryl, functionalised aryl, vinyl; X = Br, I) simultaneously promotes Schlenk equilibria (leading to competent nucleophiles) and the formation of an Al-Zn-ligand catalyst delivering 80-9