108202-35-3

Upstream product

• 135-19-3 β-naphthol 
• 875-83-2 sodium 2-naphtholate 
• 143674-28-6 10-(4'-methylphenyl)phenothiabismine 5,5-dioxide 
• 5720-05-8 4-methylphenylboronic acid 
• 573-97-7 1-bromo-2-naphthol 

Relevant academic research and scientific papers

Copper-catalyzed selective ortho-arylations of 2-naphthol and phenol derivatives with diaryliodonium salts

The selective arylations of 2-naphthol and phenol derivatives catalyzed by Cu(OTf)2 with using diaryliodonium(III) salts have been developed. With this method, biaryls bearing hydroxyl groups can be easily accessed in moderate to good yields. Additionally, this protocol provided an alternative for the preparation of 3-arylated binaphthalene derivatives.

Synthesis and reaction of unsymmetrical tetraarylbismuthonium salts. First isolation of bismuthonium salts bearing all different aryl groups

Successive treatment of triarylbismuth difluorides (1) with a Lewis acid, Me3SiCN, and aryltributylstannanes (2) in CH2Cl2 gives unsymmetrical tetraarylbismuthonium salts (3) in moderate to good yield. The migratory aptitu

Modular bismacycles for the selective C–H arylation of phenols and naphthols

Given the important role played by 2-hydroxybiaryls in organic, medicinal and materials chemistry, concise methods for the synthesis of this common motif are extremely valuable. In seeking to extend the lexicon of synthetic chemists in this regard, we have developed an expedient and general strategy for the ortho-arylation of phenols and naphthols using readily available boronic acids. Our methodology relies on in situ generation of a uniquely reactive Bi(v) arylating agent from a bench-stable Bi(iii) precursor via telescoped B–to–Bi transmetallation and oxidation. By exploiting reactivity that is orthogonal to conventional metal-catalysed manifolds, diverse aryl and heteroaryl partners can be rapidly coupled to phenols and naphthols under mild conditions. Following arylation, high-yielding recovery of the Bi(iii) precursor allows for its efficient re-use in subsequent reactions. Mechanistic interrogation of each key step of the methodology informs its practical application and provides fundamental insight into the underexploited reactivity of organobismuth compounds.

Carbon-Oxygen Homocoupling of 2-Naphthols through Electrochemical Oxidative Dearomatization

A homocoupling reaction of 2-naphthols with formation of a C-O bond through electrochemical oxidative dearomatization in the presence of catalytic amounts of ferrocene and a ruthenium complex was developed. Mechanistic studies revealed that the reaction might proceed through coupling between two identical radical species. Moreover, a gram-scale experiment was performed to illustrate the potential practicability of this methodology in organic synthesis.

Regioselective and Chemoselective Reduction of Naphthols Using Hydrosilane in Methanol: Synthesis of the 5,6,7,8-Tetrahydronaphthol Core

A regioselective and chemoselective method for catalytic synthesis of biologically interesting 5,6,7,8-tetrahydronaphthols by reduction of naphthols was described. The side aromatic hydrocarbons in naphthols were site-selectively reduced, using hydrosilanes in methanol, allowing for retaining functional phenol scaffolds intact. It presents a rare example of using low-cost and air-stable hydrosilane for catalytic reduction of unactivated aromatic hydrocarbons under mild conditions. This reaction is scalable and proceeds in high selectivity without the formation of 1,2,3,4-tetrahydronaphthol byproducts with toleration of sensitive functionalities such as bromide, chloride, fluoride, ketone, ester, and amide.

PENTAVALENT ORGANOBISMUTH REAGENTS. PART VI. COMPARATIVE MIGRATORY APTITUDES OF ARYL GROUPS IN THE ARYLATION OF PHENOLS AND ENOLS BY PENTAVALENT BISMUTH REAGENTS

The relative migratory aptitudes of p-substituted aryl groups in moving from intermediates based on pentavalent bismuth to carbon have been investigated for the typical cases of 2-naphthol and 2-carbethoxycyclohexanone.The relative rates for p-OMe, p-Me a