23096-47-1

Upstream product

• 2026-48-4 (S)-valinol 
• 347-84-2 1-(4-fluorophenyl)-2-phenylethanone 
• 31593-52-9 2-benzyl-1,3-dithiane 
• 122-78-1 phenylacetaldehyde 
• 459-57-4 4-fluorobenzaldehyde 
• 87100-28-5 pinacol benzylboronate 
• 100-39-0 benzyl bromide 
• 103-83-3 N,N'-dimethylbenzylamine 
• 6921-34-2 benzylmagnesium chloride 
• 96-09-3 styrene oxide 
• 1765-93-1 4-fluoroboronic acid 
• 1589-82-8 phenylmagnesium bromide 
• 405-99-2 para-fluorostyrene 
• 100-63-0 phenylhydrazine 

Downstream Products

• 347-84-2 1-(4-fluorophenyl)-2-phenylethanone 
• 3669-48-5 1-(4-phenoxyphenyl)-2-phenylethan-1-one 
• 1016896-36-8 (R)-1-acetoxy-2-phenyl-1-(4-fluorophenyl)ethane 

Relevant academic research and scientific papers

Four-Step Domino Reaction Enables Fully Controlled Non-Statistical Synthesis of Hexaarylbenzene with Six Different Aryl Groups**

Hexaarylbenzene (HAB) derivatives are versatile aromatic systems playing a significant role as chromophores, liquid crystalline materials, molecular receptors, molecular-scale devices, organic light-emitting diodes and candidates for organic electronics. Statistical synthesis of simple symmetrical HABs is known via cyclotrimerization or Diels–Alder reactions. By contrast, the synthesis of more complex, asymmetrical systems, and without involvement of statistical steps, remains an unsolved problem. Here we present a generally applicable synthetic strategy to access asymmetrical HAB via an atom-economical and high-yielding metal-free four-step domino reaction using nitrostyrenes and α,α-dicyanoolefins as easily available starting materials. Resulting domino product—functionalized triarylbenzene (TAB)—can be used as a key starting compound to furnish asymmetrically substituted hexaarylbenzenes in high overall yield and without involvement of statistical steps. This straightforward domino process represents a distinct approach to create diverse and still unexplored HAB scaffolds, containing six different aromatic rings around central benzene core.

Nickel-Catalyzed Cross-Coupling of Alkyl Carboxylic Acid Derivatives with Pyridinium Salts via C-N Bond Cleavage

The electrophile-electrophile cross-coupling of carboxylic acid derivatives and alkylpyridinium salts via C-N bond cleavage is developed. The method is distinguished by its simplicity and steers us through a variety of functionalized ketones in good to excellent yields. Besides acid chlorides, carboxylic acids were also employed as acylating agents, which enabled us to incorporate acid-sensitive functional groups such as MOM, BOC, and acetal. Control experiments with TEMPO revealed a radical pathway.

Visible-Light-Driven External-Reductant-Free Cross-Electrophile Couplings of Tetraalkyl Ammonium Salts

Cross-electrophile couplings between two electrophiles are powerful and economic methods to generate C-C bonds in the presence of stoichiometric external reductants. Herein, we report a novel strategy to realize the first external-reductant-free cross-electrophile coupling via visible-light photoredox catalysis. A variety of tetraalkyl ammonium salts, bearing primary, secondary, and tertiary C-N bonds, undergo selective couplings with aldehydes/ketone and CO2. Notably, the in situ generated byproduct, trimethylamine, is efficiently utilized as the electron donor. Moreover, this protocol exhibits mild reaction conditions, low catalyst loading, broad substrate scope, good functional group tolerance, and facile scalability. Mechanistic studies indicate that benzyl radicals and anions might be generated as the key intermediates via photocatalysis, providing a new direction for cross-electrophile couplings.

Chemoselective Benzylation of Aldehydes Using Lewis Base Activated Boronate Nucleophiles

A benzylation of aldehydes using primary and secondary benzylboronic acid pinacol esters is reported. Activation of the boronic ester with s-butyllithium rendered it nucleophilic toward aldehydes. The activated nucleophile chemoselectively transfers the benzyl group over the sec-butyl group, providing excellent yields of the benzylated products. 11B NMR experiments were performed to study the mechanism of this transformation.

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.

Exploring Tandem Ruthenium-Catalyzed Hydrogen Transfer and SNAr Chemistry

A hydrogen-transfer strategy for the catalytic functionalization of benzylic alcohols via electronic arene activation, accessing a diverse range of bespoke diaryl ethers and aryl amines in excellent isolated yields (38 examples, 70% average yield), is reported. Taking advantage of the hydrogen-transfer approach, the oxidation level of the functionalized products can be selected by judicious choice of simple and inexpensive additives.

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.

An unusual chemoselective oxidation strategy by an unprecedented exploration of an electrophilic center of DMSO: A new facet to classical DMSO oxidation

A conceptually new dimethyl sulfoxide (DMSO) based oxidation process without the use of any activator has been demonstrated for the oxidation of active methylenes and benzhydrols. The developed protocol utilizes the electrophilic center of DMSO for oxidation, which was unexplored before. Mechanistic investigation has confirmed that the source of oxygen is DMSO.

Catalyst-controlled highly selective coupling and oxygenation of olefins: A direct approach to alcohols, ketones, and diketones

Oxygen? That's radical! A method for the direct synthesis of substituted alcohols, ketones, and diketones through a catalyst-controlled highly chemoselective coupling and oxygenation of olefins has been developed. The method is simple and practical, can be switched by the selection of different catalysts, and employs molecular oxygen as both an oxidant and a reagent. Copyright

The dual role of ruthenium and alkali base catalysts in enabling a conceptually new shortcut to N-unsubstituted pyrroles through unmasked α-amino aldehydes

A virtually salt-free and straightforward bimolecular assembly giving N-unsubstituted pyrroles through fully unmasked α-amino aldehydes, which was enabled by the dual effects of a catalytic ruthenium complex and an alkali metal base, is reported. Either solvent-free or acceptorless dehydrogenation facilitates high atom, step, and pot economy, which are otherwise difficult to achieve in multistep operations involving protection/deprotection.