858035-58-2

Upstream product

• 2142-69-0 2-bromophenyl methyl ketone 
• 13922-41-3 1-Naphthylboronic acid 
• 2142-68-9 1-(2-chlorophenyl)ethanone 
• 91-58-7 2-chloronaphthalene 
• 2743-00-2 (E)-4-methoxy-N-(1-phenylethylidene)benzenamine 
• 90-13-1 1-Chloronaphthalene 
• 703-55-9 1-naphthylmagnesiumbromide 

Downstream Products

• 52086-07-4 7-methyl-7H-benzo[c]fluorine 
• 1449316-19-1 (E)-1-(2-(naphthalen-1-yl)phenyl)ethanone O-acetyl oxime 
• 1449316-20-4 (Z)-1-(2-(naphthalen-1-yl)phenyl)ethanone O-acetyl oxime 

Relevant academic research and scientific papers

Stereodynamics and edge-to-face CH-π aromatic interactions in o-phenethyl-substituted biaryls

As part of a search for systems that exhibit intramolecular aromatic edge-to-face interactions, a series of four biaryl compounds containing a phenethyl side chain were prepared. These compounds exist as a slowly interconverting mixture of two atropisomer

N-Iodosuccinimide and dioxygen in an air-enabled synthesis of 10-phenanthrenols under sunlight

Using a catalytic amount ofN-iodosuccinimide (NIS) in combination with O2in air, an aerobic oxidative reaction was carried out to efficiently and scalably construct a series of 10-phenanthrenols under sunlight at room temperature. Mechanistic studies reveal that H2O2generatedin situwas responsible for the conversion of I2to IOH as a potential initiator for later catalytic cycle.

Non-c2-symmetric bis-benzimidazolium salt applied in the synthesis of sterically hindered biaryls

A novel non-C2-symmetric bis-benzimidazolium salt derived from (±)-valinol has been prepared by a simple and straightforward process in good yield. The structure of bis-benzimidazolium salt provided a bulky steric group on the ethylene bridge; which facilitates the catalytic efficacy in the C(sp2 )–C(sp2 ) formation. Its catalytic activity in Suzuki–Miyaura cross-coupling reaction of unactivated aryl chlorides has been found to have high efficacy in 1 mol% Pd loading. This protocol demonstrated the potential on the synthesis of sterically hindered biaryls.

Photoredox/Cobalt-Catalyzed C(sp3)-H Bond Functionalization toward Phenanthrene Skeletons with Hydrogen Evolution

The first example of photoredox strategy for synthesis of phenanthrene skeletons through C(sp3)-H functionalization under external oxidant-free conditions is achieved. This transformation relies on the keto-enol tautomerism of 1,3 dicarbonyl moiety, i.e., the enol form of 1,3-dicarbonyl derivatives with relatively lower oxidation potential can be activated by the excited acridinium photocatalyst. The electron and proton eliminated from the substrate are immediately captured by a cobaloxime catalyst to exclusively afford a-carbonyl radical for highly substituted 10-phenanthrenols in good to excellent yields.

N-Bromosuccinimide-Induced C-H Bond Functionalization: An Intramolecular Cycloaromatization of Electron Withdrawing Group Substituted 1-Biphenyl-2-ylethanone for the Synthesis of 10-Phenanthrenol

An NBS-induced intramolecular cycloaromatization for the synthesis of 10-phenanthrenols from electron-withdrawing group substituted 1-biphenyl-2-ylethanones is described. The in situ generated bromide was designed to act as an initiator for the radical C-H bond activation. An oxidative cross-dehydrogenative coupling reaction of a highly active C-H bond with an inert C-H bond readily occurs under mild conditions without the need for transition metals or strong oxidants.

Pd(II) complexes of Schiff bases and their application as catalysts in Mizoroki-Heck and Suzuki-Miyaura cross-coupling reactions

Schiff bases of 2-(phenylthio)aniline, (C6H5)SC6H4N=CR (R=(o-CH3)(C6H5), (o-OCH3)(C6H5) or (o-CF3)(C6H5)), and their palladium complexes (PdLCl2) were synthesized. The compounds were characterized using 1H NMR and 13C NMR spectroscopy and micro analysis. Also, electrochemical properties of the ligands and Pd(II) complexes were investigated in dimethylformamide-LiClO4 solution with cyclic and square wave voltammetry techniques. The Pd(II) complexes showed both reversible and quasi-reversible processes in the -1.5 to 0.3V potential range. The synthesized Pd(II) complexes were evaluated as catalysts in Mizoroki-Heck and Suzuki-Miyaura cross-coupling reactions.

Cobalt-catalyzed ortho -arylation of aromatic imines with aryl chlorides

An ortho-arylation reaction of aromatic imines with aryl chlorides has been achieved using a cobalt-N-heterocyclic carbene catalyst in combination with a neopentyl Grignard reagent. The reaction takes place at room temperature to afford biaryl products in moderate to good yields.

Cobalt-catalyzed cross-coupling reactions of heterocyclic chlorides with arylmagnesium halides and of polyfunctionalized arylcopper reagents with aryl bromides, chlorides, fluorides and tosylates

A range of aromatic organocopper or organomagnesium compounds undergo smooth cross-coupling reactions with aryl bromides, chlorides, fluorides and tosylates, leading to polyfunctionalized aromatics or heterocycles in the presence of cobalt salts (5-7.5 mol%) as catalysts. Very mild reaction conditions are needed and, in the case of cross-coupling with organocopper compounds, Bu4NI (1 equiv) and 4-fluorostyrene (20 mol%) are essential as promoters for successful couplings. Georg Thieme Verlag Stuttgart.

Cobalt(II)-catalyzed cross-coupling of polyfunctional aryl copper reagents with aryl bromides and chlorides

(Chemical Equation Presented) Polyfunctionalized biphenyl and heteroaromatic compounds were formed in the presence of [Co(acac)2], Bu4Nl, and 4-fluorostyrene (3) through a smooth cross-coupling reaction between organocopper reagents 1, prepared by the transmetalation of functionalized aryl magnesium halides with CuCN·2 LiCl, and aryl halides 2 that bear electron-withdrawing substituents. acac = acetylacetonate, DME = 1,2-dimethoxyethane, DMPU = 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone.