108202-36-4

Upstream product

• 696-62-8 para-iodoanisole 
• 15147-55-4 2-naphtholate 
• 36294-21-0 potassium 2-naphthoxide 
• 573-97-7 1-bromo-2-naphthol 
• 5720-07-0 4-methoxyphenylboronic acid 
• 135-19-3 β-naphthol 
• 1017246-79-5 10-(4-methoxyphenyl)phenothiabismine 5,5-dioxide 
• 100-66-3 methoxybenzene 
• 773-90-0 1-diazo-2(1H)naphthalenone 

Downstream Products

• 28656-26-0 3,3-Bis(4-methoxyphenyl)[3H]naphtho[2,1-b]pyran 

Relevant academic research and scientific papers

Regioselective Construction of Functionalized Biarylols by Fe(OTf)3-Catalyzed Direct Arylation of 1-Diazonaphthalen-2(1H)-ones and Their Fluorescence Properties

A facile and efficient protocol for the construction of functionalized biarylols by Fe(OTf)3-catalyzed direct arylation of 1-diazonaphthalen-2(1H)-ones with arenes has been developed. This methodology provides diverse 1-arylnaphthalen-2-ols in moderate to good yields. This approach has also been applied to the synthesis of biologically interesting polycyclic-aromatic-substituted and heteroaryl-substituted naphthalen-2-ols. The synthesized compounds bearing an anthracene scaffold can be useful as potential fluorescent biomarkers for confocal imaging of clone cells.

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.

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.

Steric effects of nucleophile-radical coupling reaction. Determination of rate constants for the reaction of aryl radicals with 2-naphthoxide anion

The absolute rate constants for the reaction of different aryl radicals with 2-naphthoxide anion were determined using an indirect method, a competition of the coupling reaction with the H-atom abstraction. We here show that the radical-ambident nucleophi

Observations on the synthesis of photochromic naphthopyrans

1-Naphthol reacts with 1,1-diarylprop-2-yn-1-ols 5a,b, under alumina catalysis, by two pathways to give the photochromic naphtho[1,2-b]pyrans 6a,b, together with the propenylidenenaphthalenones 7a,b, representatives of a new class of merocyanine dyes. With 2-methyl-1-naphthol, formation of the photochrome is suppressed; the only products are merocyanines 7c,d. The cyclocondensation of 2-naphthol with 5a,b proceeds much more efficiently, to give the naphtho[2,1-b]pyrans 14a,b. Pyran formation is not suppressed from either 1-bromo- or 1-(4 -methoxyphenyl)-2-naphthol; reaction with 5a,b merely results in expulsion of the C-1 substituent. An alternative pathway supervenes in the reaction of 1-methyl-2-naphthol with 5a to give the benz[e]indanone 17, the constitution of which was determined by X-ray crystallography. Reaction of the 1,3,3-triarylpropynols 19a,b with 1-naphthol affords the naphthopyrans 20 together with merocyanines 21, whilst the isomeric pyrans 23 are efficiently produced from 2-naphthol. The configuration of merocyanines 7a and 21a was unequivocally established by X-ray crystallography. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.

Regiochemistry of the Coupling of Aryl Radicals with Nucleophiles Derived from the Naphthyl System. Experimental and Theoretical Studies

We here report the photostimulated reaction of unactived aromatic halides with ambident nucleophiles derived from the naphthyl system such as 1- and 2-naphthylamide, 2-naphthoxide, 2-naphthalenethiolate, and 2 naphthaleneselenate ions, by the SRN1 mechanism of nucleophilic substitution.According to our experimental results, C-arylation in position 1 of the naphthyl moiety is the only reaction observed with 2-naphthoxide ions and it is favored over N-arylation with 1- and 2-naphthylamide ions.Heteroatom arylation is preferred over C-arylation with 2-naphthalenethiolate ions while it is the only observed reaction with 2-naphthaleneselenate ions.A theoretical study was carried out to explain the regiochemistry of the system.In competition experiments, 2-naphthalenethiolate ions proved to be 1.8 +/- 0.2 times more reactive than 2-naphthoxide ions for C-substitution toward p-anisyl radicals in liquid ammonia.

PHOTOSTIMULATED REACTION OF ARYL IODIDES WITH 2-NAPHTHOXIDE IONS BY THE SRN1 MECHANISM

The photostimulated reactions of p-iodoanisole (2) and 1-iodonaphthalene (7) with 2-naphthoxide ions in liquid ammonia gave the corresponding 1-aryl-2-naphthols as the only substitution product.These reactions are proposed to proceed via the SRN1 mechanism for nucleophilic aromatic substitution.

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