136374-31-7

Upstream product

• 135-19-3 β-naphthol 
• 573-97-7 1-bromo-2-naphthol 
• 128796-39-4 4-trifluoromethylphenylboronic acid 
• 402-43-7 p-trifluoromethylphenyl bromide 

Relevant academic research and scientific papers

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.

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.

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.

RuII-catalyzed vinylative dearomatization of naphthols via a C(sp2)-H bond activation approach

Intermolecular annulation reactions of 1-aryl-2-naphthols with internal alkynes proceed efficiently in the presence of a Ru catalyst and a Cu oxidant to generate spirocyclic compounds by sequential cleavage of the C(sp 2)-H bond, migratory insertion of the alkyne, and dearomatization of the naphthyl ring. Various spirocyclic molecules bearing an all-carbon quaternary stereocenter could be obtained by this novel method with good yields and excellent regioselectivity, and the current process tolerates a variety of synthetically important functional groups.

Synthesis of fluorinated biaryl derivatives via SRN1 reactions

Flourinated biaryl derivatives Y-C6-H4-ArOH (Y = F, CF3, OCF3) are obtained by coupling Y-C6-H4-Br(p) with anions derived from ArOH via a photostimulated SRN1 reaction.