118693-55-3

Upstream product

• 135-19-3 β-naphthol 
• 573-97-7 1-bromo-2-naphthol 
• 126747-14-6 4-cyanophenylboronic acid 
• 111278-47-8 C₁₃H₉N₃S 
• 127703-34-8 tetrabutylammonium β-naphthoxide 
• 132555-11-4 (E)-(4-Cyanophenyl)azo phenyl sulfide 
• 29577-88-6 (Z)-tert-Butyl (4-cyanophenyl)azo sulfide 
• 623-00-7 4-bromobenzenecarbonitrile 

Relevant academic research and scientific papers

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.

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.

SRN1C-arylation of potassium aryloxides by arylazo phenyl or tert- butyl sulfides in DMSO

Aryloxide ions (Ar′O-) behave as C-nucleophiles towards diazosulfides (ArN = NSR; R = Ph, But) leading to imsymmetrical hydroxybiaryls (ArAr′OH) via C-C coupling. The reaction is particularly suited for the synthesis of terms which contain electron-withdrawing groups on the Ar moiety. The SRN1 mechanism is proposed on the grounds of experimental evidences.

UNSYMMETRICAL BIARYLS FROM ARYLOXIDE ANIONS AND ARYLAZO PHENYL SULFIDES IN DMSO.

Carbon-arylation of phenoxide and naphthoxide anions by arylazo phenyl sulfides represents a convenient synthesis of unsymmetrically substituted hydroxybiaryls.

PHENOXIDE AND NAPHTHOXIDE IONS AS NUCLEOPHILES FOR SRN1 REACTIONS: SYNTHESIS OF BIPHENYL AND PHENYLNAPHTHYL DERIVATIVES

Biphenyl or phenylnaphthyl derivatives are obtained by photostimulated SRN1 reactions between the anion of phenols or naphthols and variously substituted haloarenes.