13391-47-4

Upstream product

• 623-03-0 4-Cyanochlorobenzene 
• 100-52-7 benzaldehyde 
• 623-00-7 4-bromobenzenecarbonitrile 
• 3058-39-7 4-iodobenzonitrile 
• 105-07-7 4-cyanobenzaldehyde 
• 98-80-6 phenylboronic acid 
• 126747-14-6 4-cyanophenylboronic acid 
• 2996-92-1 phenyl trimethylsiloxane 
• 100-58-3 phenylmagnesium bromide 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 100-51-6 benzyl alcohol 
• 591-50-4 iodobenzene 
• 623-26-7 terephthalonitrile 
• 591-51-5 phenyllithium 

Downstream Products

• 1313757-11-7 1-(bis(4-iodophenyl)methyl)-1H-1,2,4-triazole 
• 1503-49-7 p-cyanobenzophenone 
• 23450-31-9 4-benzylbenzonitrile 
• 308110-05-6 4-(phenyl-piperazin-1-yl-methyl)-benzonitrile 
• 51747-58-1 4-(4-Phenylbenzoyl)benzhydrol 
• 13391-42-9 4-Cyan-benzhydrylchlorid 

Relevant academic research and scientific papers

Heterogeneous Photocatalysis of Poly(4-trifluoromethylpyridine-2,6-diyl)

Poly(4-trifluoromethylpyridine-2,6-diyl) shows heterogeneous photocatalysis under visible light (λ>400 nm), leading to efficient reductions not only of water to H2 but also of some carbonyl compounds to alcohols in the presence of triethylamine as a sacrificial electron donor.

Synthesis of Polyfunctional Diorganomagnesium and Diorganozinc Reagents through In Situ Trapping Halogen–Lithium Exchange of Highly Functionalized (Hetero)aryl Halides in Continuous Flow

We report a halogen–lithium exchange performed in the presence of various metal salts (ZnCl2, MgCl2?LiCl) on a broad range of sensitive bromo- or iodo(hetero)arenes using BuLi or PhLi as the exchange reagent and a commercially available continuous-flow setup. The resulting diarylmagnesium or diarylzinc species were trapped with various electrophiles, resulting in the formation of polyfunctional (hetero)arenes in high yields. This method enables the functionalization of (hetero)arenes containing highly sensitive groups such as an isothiocyanate, nitro, azide, or ester. A straightforward scale-up was possible without further optimization.

Efficient Visible-light-driven Photocatalysis. Poly(pyridine-2,5-diyl)-catalysed Hydrogen Photoevolution and Photoreduction of Carbonyl Compounds

Poly(pyridine-2,5-diyl), an insoluble yellow powder, shows efficient photocatalysis under visible light (λ>400 nm) towards water and some carbonyl compounds in the presence of triethylamine as a sacrificial electron donor, yielding H2 and corresponding alcohols, respectively.

INHIBITORS OF ANTIGEN PRESENTATION BY HLA-DR

Chromanone compounds, pharmaceutical compositions containing them, methods of making them, and methods of using them including methods for treating disease states, disorders, and conditions associated with the inhibition of antigen presentation by HLA-DR.

Electrochemical Arylation of Aldehydes, Ketones, and Alcohols: from Cathodic Reduction to Convergent Paired Electrolysis

Arylation of carbonyls, one of the most common approaches toward alcohols, has received tremendous attention, as alcohols are important feedstocks and building blocks in organic synthesis. Despite great progress, there is still a great gap to develop an ideal arylation method featuring mild conditions, good functional group tolerance, and readily available starting materials. We now show that electrochemical arylation can fill the gap. By taking advantage of synthetic electrochemistry, commercially available aldehydes (ketones) and benzylic alcohols can be readily arylated to provide a general and scalable access to structurally diverse alcohols (97 examples, >10 gram-scale). More importantly, convergent paired electrolysis, the ideal but challenging electrochemical technology, was employed to transform low-value alcohols into more useful alcohols. Detailed mechanism study suggests that two plausible pathways are involved in the redox neutral α-arylation of benzylic alcohols.

Reductive arylation of aliphatic and aromatic aldehydes with cyanoarenes by electrolysis for the synthesis of alcohols

An electroreductive arylation reaction of aliphatic and aromatic aldehydes as well as ketones with electro-deficient (hetero)arenes is described. A variety of cyano(hetero)arenes and carbonyl compounds, especially aliphatic aldehydes, have been examined, providing secondary and tertiary alcohols in moderate to good yields. Mechanistic studies, including cyclic voltammetry (CV), electron paramagnetic resonance (EPR), and divided-cell experiments, support the generation of aliphatic ketyl radicals and persistent heteroaryl radical anions via cathodic reduction followed by radical-radical cross-coupling.

Dual-Role Catalysis by Thiobenzoic Acid in Cα-H Arylation under Photoirradiation

Thiobenzoic acid (TBA) can serve as a single-electron reducing agent under photoirradiation from a blue light-emitting diode, in the presence of appropriate electron acceptors, and the resulting sulfur-centered radical species undergoes hydrogen atom abstraction. This dual-role catalysis by TBA enables regioselectivie Cα-H arylation of benzylamines, benzyl alcohols, and ethers, as well as dihydroimidazoles, with cyano(hetero)arenes in good yield, without the need for a transition-metal photocatalyst and/or synthetically elaborated organic dyes.

Reaction of Diisobutylaluminum Borohydride, a Binary Hydride, with Selected Organic Compounds Containing Representative Functional Groups

The binary hydride, diisobutylaluminum borohydride [(iBu)2AlBH4], synthesized from diisobutylaluminum hydride (DIBAL) and borane dimethyl sulfide (BMS) has shown great potential in reducing a variety of organic functional groups. This unique binary hydride, (iBu)2AlBH4, is readily synthesized, versatile, and simple to use. Aldehydes, ketones, esters, and epoxides are reduced very fast to the corresponding alcohols in essentially quantitative yields. This binary hydride can reduce tertiary amides rapidly to the corresponding amines at 25 °C in an efficient manner. Furthermore, nitriles are converted into the corresponding amines in essentially quantitative yields. These reactions occur under ambient conditions and are completed in an hour or less. The reduction products are isolated through a simple acid-base extraction and without the use of column chromatography. Further investigation showed that (iBu)2AlBH4 has the potential to be a selective hydride donor as shown through a series of competitive reactions. Similarities and differences between (iBu)2AlBH4, DIBAL, and BMS are discussed.

Bulky N-Heterocyclic-Carbene-Coordinated Palladium Catalysts for 1,2-Addition of Arylboron Compounds to Carbonyl Compounds

The synthesis of primary, secondary, and tertiary alcohols by the 1,2-addition of arylboronic acids or boronates to carbonyl compounds, including unactivated ketones, using novel bulky yet flexible N-heterocyclic carbene (NHC)-coordinated 2,6-di(pentan-3-yl)aniline (IPent)-based cyclometallated palladium complexes (CYPs) as catalysts is reported. The PhS-IPent-CYP-catalyzed reactions are efficient at low catalyst loadings (0.02–0.3 mol% Pd), and the exceptional catalytic activity for 1,2-addition is attributed to the steric bulk of the NHC ligand. These reactions can yield a wide range of functionalized benzylic alcohols that are difficult to synthesize by classical protocols using highly active organomagnesium or lithium reagents.

Nickel Catalyzed Intermolecular Carbonyl Addition of Aryl Halide

In this study, we develop a nickel-catalyzed carbonyl arylation reaction employing aldehydes with aryl and allyl halides. Various aryl, α,β-unsaturated aldehyde and aliphatic aldehydes can be converted into their corresponding secondary alcohols in moderate-to-high yields. In addition, we extended this approach to develop an asymmetric reductive coupling reaction that combines nickel salts with chiral bisoxazoline ligands to give secondary alcohols with moderate enantioselectivity.