67035-92-1

Upstream product

• 92-52-4 biphenyl 
• 2719-27-9 cyclohexanylcarbonyl chloride 
• 5122-94-1 4-biphenylboronic acid 
• 74628-02-7 C₁₁H₂₁O₅P 
• 110-82-7 cyclohexane 
• 14002-51-8 4-biphenyl-carboxylic acid chloride 
• 92867-95-3 [1,1'-biphenyl]-4-yl(1H-imidazol-1-yl)methanone 
• 92-66-0 4-bromo-1,1'-biphenyl 
• 2043-61-0 cyclohexanecarbaldehyde 

Downstream Products

• 410534-87-1 4'-cyclohexanoylbiphenyl-4-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Light-DrivenN-Heterocyclic Carbene Catalysis Using Alkylborates

Radical-radical coupling, the selective reaction between two different radical species, has contributed to the methodology for connecting bulky units. Light-drivenN-heterocyclic carbene (NHC) organocatalysis is recognized as a state-of-the-art methodology enabling radical-radical coupling. The catalytic process involves forming an acyl azolium intermediate from the NHC catalyst and an acyl donor, followed by single electron reduction of this key intermediate, which is largely dependent on the photoredox catalyst. We designed a radical NHC catalysis in which the direct photoexcitation of a borate to form a high reducing agent facilitated the single electron reduction event. The borate produces an alkyl radical for the single electron transfer process to accomplish the radical-radical coupling. This protocol enables cross-coupling between alkylborates and acyl imidazoles in addition to radical relay-type alkylacylations of alkenes with alkylborates and acyl imidazoles, affording ketones with a broad scope.

Rapid and Direct Photocatalytic C(sp3)?H Acylation and Arylation in Flow

Herein, we report a photocatalytic procedure that enables the acylation/arylation of unfunctionalized alkyl derivatives in flow. The method exploits the ability of the decatungstate anion to act as a hydrogen atom abstractor and produce nucleophilic carbon-centered radicals that are intercepted by a nickel catalyst to ultimately forge C(sp3)?C(sp2) bonds. Owing to the intensified conditions in flow, the reaction time can be reduced from 12–48 hours to only 5–15 minutes. Finally, kinetic measurements highlight how the intensified conditions do not change the reaction mechanism but reliably speed up the overall process.

Direct C-H Arylation of Aldehydes by Merging Photocatalyzed Hydrogen Atom Transfer with Palladium Catalysis

Herein, we report that merging palladium catalysis with hydrogen atom transfer (HAT) photocatalysis enabled direct arylations and alkenylations of aldehyde C-H bonds, facilitating visible light-catalyzed construction of a variety of ketones. Tetrabutylammonium decatungstate and anthraquinone were found to act as synergistic HAT photocatalysts. Density functional theory calculations suggested a Pd0-PdII-PdIII-PdI-Pd0 pathway and revealed that regeneration of the Pd0 catalyst and the photocatalyst occurs simultaneously in the presence of KHCO3. This regeneration features a low energy barrier, promoting efficient coupling of the palladium catalytic cycle with the photocatalytic cycle. The work reported herein suggests great promise for further applications of HAT photocatalysis in palladium-catalyzed cross-coupling and C-H functionalization reactions to be successful.

Carboxylic phosphoric anhydrides as a new coupling partner in Pd-catalyzed coupling reactions: A new ketone synthesis

The Pd-catalyzed cross-coupling reactions of carboxylic phosphoric anhydrides with organoboronic acids or organostannanes afforded the corresponding ketones. The intramolecular Heck reaction was successful with carboxylic phosphoric anhydrides as a coupling partner. Georg Thieme Verlag Stuttgart.

5-Phenyl substituted 1-methyl-2-pyridones and 4′-substituted biphenyl-4-carboxylic acids. synthesis and evaluation as inhibitors of steroid-5α-reductase type 1 and 2

The synthesis of a series of 5-phenyl substituted 1-methyl-2-pyridones (I) and 4′-substituted biphenyl-4-carboxylic acids (II) as novel A-C ring steroidomimetic inhibitors of 5α-reductase (5αR) is described. Compounds 1-4 (I) were synthesized by palladium catalyzed cross coupling (Ishikura) reaction between diethyl(3-pyridyl)borane and aryl halides (1b-4b) followed by α-oxidation with sodium ferrocyanate of the 1-methyl-pyridinium salt. Inhibitors II (5-18) were obtained either by two successive Friedel-Crafts acylations from biphenyl (5a-10a) followed by saponification to yield the corresponding carboxylic acids (5-10) or by Suzuki cross coupling reaction to give the 4′-substituted biphenyl 1-4-carbaldehydes 11a-18a. The latter compounds were subjected to a Lindgren oxidation to yield compounds 11-18. The compounds were tested for inhibitory activity toward human and rat 5 αR1 and 2. The test compounds inhibited 5αR, showing a broad range of inhibitory potencies. The best compound in series I was the N-(dicyclohexyl)-4-(1,2-dihydro-1-methyl-2-oxopyrid-5-yl) benzamide 4 exhibiting an IC50 value for the human type 2 enzyme of 10 μM. In series II, the most active compound toward human type 2 isozyme was the 4′-(dicyclohexyl)acetyl-4-biphenyl carboxylic acid (10; IC50 = 220 nM). Both series showed only marginal activity toward the human type 1 isozyme. In conclusion, the biphenyl carboxylic acids (II) are more appropiate for 5αR inhibition than the 5-phenyl-1-methyl-2-pyridones (1). Especially the 4′-carbonyl compounds 5-10 represent new lead structures for the development of novel human type 2 inhibitors. Copyright