136374-30-6

Upstream product

• 135-19-3 β-naphthol 
• 460-00-4 1-Bromo-4-fluorobenzene 
• 1765-93-1 4-fluoroboronic acid 
• 573-97-7 1-bromo-2-naphthol 

Relevant academic research and scientific papers

Resin-bound triaryl bismuthanes and bismuth diacetates: Novel multidirectional linkers and novel resin-bound arylation reagents

A general synthesis of resin-bound triaryl bismuthanes and resin-bound triaryl bismuth diacetates starting from commercially available chloromethyl polystyrene is reported. For the first time resin-bound bismuth has been utilized as part of a multidirectional linker system for solid-phase organic synthesis and as a resin-bound arylation reagent.

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.

Transition-Metal-Free Aryl–Aryl Cross-Coupling: C?H Arylation of 2-Naphthols with Diaryliodonium Salts

Transition-metal-free regioselecitive C?H arylation of 2-naphthols with diaryliodonium salts has been developed. The reaction proceeds under very simple experimental conditions and affords a range of products with various substitution patterns. The method allows for the incorporation of electron-deficient aryls, which complements well currently existing metal-free aryl–aryl cross-couplings of phenols that have been so far restricted to the introduction of electron-rich aryl moieties. The mechanism of the reaction was studied by means of DFT calculations, demonstrating that the C?C bond formation occurs via a dearomatization of 2-naphthol substrate, followed by a subsequent rearomatization by tautomerization. The computations show that the use of a low polarity solvent and an insoluble inorganic base is key to securing the high selectivity of the C?C coupling over a competing C?O arylation pathway, by preventing the incipient deprotonation of 2-naphthol.

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 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.