84812-40-8

Upstream product

• 66-77-3 1-naphthaldehyde 
• 556-56-9 allyl iodid 
• 925-90-6 ethylmagnesium bromide 
• 2386-64-3 ethylmagnesium chloride 
• 1233-36-9 (E)-1,2-bis(1-naphthyl)ethene 
• 941-98-0 1'-naphthacetophenone 
• 3457-41-8 1,2-bis(naphthalen-1-yl)ethane-1,2-dione 

Downstream Products

• 86-55-5 1-naphthalenecarboxylic acid 
• 66-77-3 1-naphthaldehyde 
• 159406-53-8 (R,R)-(+)-1,2-di-naphthalen-1-yl-ethane-1,2-diol 
• 229184-99-0 1,2-di(1-naphthyl)ethane-1,2-diol 

Relevant academic research and scientific papers

Application of coumarin dyes for organic photoredox catalysis

Here we report the application of readily prepared and available coumarin dyes for photoredox catalysis, which are able to mimic powerful reductant [Ir(iii)] complexes. Coumarin derivatives 9 and 10 were employed as photoreductants in pinacol coupling and in other reactions, in the presence of Et3N as a sacrificial reducing agent. As the electronic, photophysical, and steric properties of coumarins could be varied, a wide applicability to several classes of photoredox reactions is predicted.

Hydrogen Bonding-Assisted Enhancement of the Reaction Rate and Selectivity in the Kinetic Resolution of d,l-1,2-Diols with Chiral Nucleophilic Catalysts

An extremely efficient acylative kinetic resolution of d,l-1,2-diols in the presence of only 0.5 mol% of binaphthyl-based chiral N,N-4-dimethylaminopyridine was developed (selectivity factor of up to 180). Several key experiments revealed that hydrogen bonding between the tert-alcohol unit(s) of the catalyst and the 1,2-diol unit of the substrate is critical for accelerating the rate of monoacylation and achieving high enantioselectivity. This catalytic system can be applied to a wide range of substrates involving racemic acyclic and cyclic 1,2-diols with high selectivity factors. The kinetic resolution of d,l-hydrobenzoin and trans-1,2-cyclohexanediol on a multigram scale (10 g) also proceeded with high selectivity and under moderate reaction conditions: (i) very low catalyst loading (0.1 mol%); (ii) an easily achievable low reaction temperature (0 °C); (iii) high substrate concentration (1.0 M); and (iv) short reaction time (30 min). (Figure presented.).

First pinacol coupling in emulsified water: Key role of surfactant and impact of alternative activation technologies

For the first time, the influence of surfactants on the radical pinacol coupling reaction is investigated. The rate and selectivity of this reductive C-C coupling are compared under three different activation technologies: thermal activation, microwave irradiation, and sonication. The use of IgepalCO520, a neutral surfactant, led to the successful conversion of aromatic or α,β-unsaturated aliphatic carbonyl compounds in moderate to excellent yield (55-90 %). An insight on the potential mechanism involved in the reaction is also proposed, based on microscopic observations and particle size measurement.

Selective Pinacol Coupling on Regeneratable Supported Acids in Sole Water

Efficient pinacol coupling was developed in sole water, using a reusable heterogeneous supported acid source and zinc as cheap available metal source. This medium can be easily regenerated up to 10-fold without loss of activity. Moreover, supported acids enhance the selectivity of the pinacol coupling reaction compared with homogeneous acids.

Enantioselective oxidation of 1,2-diols with quinine-derived urea organocatalyst

Quinine-derived urea has been identified as a highly efficient organocatalyst for the enantioselective oxidation of 1,2-diols using bromination reagents as the oxidant. This simple procedure utilizes readily available reagents and operates at ambient temperature to yield a wide range of α-hydroxy ketones in good yield (up to 94%) and excellent enantioselectivity (up to 95% ee).

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.

Catalytic asymmetric alkylation of aldehydes with Grignard reagents

(Chemical Equation Presented) Added benefits: Grignard reagents can be employed in the asymmetric alkylation of aldehydes by using a titanium(IV) catalyst derived from binol in the presence of excess titanium tetraisopropoxide (see scheme). The reaction proceeds with a low catalyst loading (2 mol%) and exhibits high enantioselectivity for both aromatic and unsaturated aldehydes and for both alkyl and aryl Grignard reagents.

Magnesium-induced pinacol coupling of aromatic aldehydes and ketones under ultrasound irradiation

The system of magnesium and magnesium iodide can reduce some aromatic aldehydes and ketones to the corresponding pinacols in good yields within 10-60 min at room temperature under ultrasound irradiation. Copyright Taylor & Francis, Inc.

Titanium(IV) iodide promoted pinacol coupling

Pinacol coupling of aromatic aldehydes was efficiently promoted by titanium tetraiodide in propionitrile to give the 1,2-diol derivatives with high dl-selectivities in high yields.

Highly diastereoselective pinacol coupling of aldehydes catalyzed by titanium-schiff base complexes

A new effective methodology for a highly diastereoselective pinacol coupling of aldehydes is described. The method employes 3 mol % of a complex prepared in situ from TiCl4(THF)2 and a Schiff base in acetonitrile. The catalytic cycle is realized with Me3SiCl and Mn as reducing agent. The dependence of the diastereoselectivity on the Schiff base used is reported.