18795-02-3

Upstream product

• 93531-00-1 1-Bromo-naphthalene-2-carboxylic acid (2-hydroxy-1,1-dimethyl-ethyl)-amide 
• 13922-41-3 1-Naphthylboronic acid 
• 90-11-9 1-Bromonaphthalene 
• 883-21-6 1-methoxy-2-naphthoic acid 
• 574-97-0 1-fluoronaphthalene-2-carboxylic acid 
• 2216-69-5 1-Methoxynaphthalene 
• 321-38-0 1-Fluoronaphthalene 
• 76373-11-0 1-bromo-2-naphthoyl chloride 
• 20717-79-7 1-bromo-2-naphthoic acid 
• 80409-67-2 1-(1-naphthyl)-naphthalene-2-carbaldehyde 
• 80373-29-1 (-)-2-<2-(1-(3R,4S,8R,9S)-quinidinoxynaphthyl)>-4,4-dimethyl-Δ²-oxazoline 
• 80325-17-3 (+)-2-<2-(1-(3R,4S,8S,9R)-quininoxynaphthyl)>-4,4-dimethyl-Δ²-oxazoline 
• 78265-10-8 2-<2-(1-methoxynaphthyl)>-4,4-dimethyl-Δ²-oxazoline 
• 78265-35-7 N-(2-Methyl-2-propan-1-ol)-1-methoxy-2-naphthalenecarboxamide 

Relevant academic research and scientific papers

Chiral Ligand-Mediated Nucleophilic Aromatic Substitution of Naphthoic Acids: A Fast and Efficient Access to Axially Chiral Biaryls

A transition metal-free synthesis of enantioenriched biaryls from aryllithium species has been developed. This approach relies on atropoenantioselective nucleophilic aromatic substitution (SNAr) reaction of unprotected naphthoic acids. The ability of a diverse set of chiral ligands to mediate this transformation has been investigated. 1,2-diether ligands outperform their diamine counterparts and the best enantiocontrol was obtained with readily accessible enantiopure trans-1,2-dimethoxycyclohexane. This SNAr reaction offers an efficient and rapid access to enantioenriched binaphthalenes, phenylnaphthalene, and phenanthrylnaphthalenes (up to 94:6 er).

Michael Reaction Inspired Atroposelective Construction of Axially Chiral Biaryls

The first copper-catalyzed atroposelective Michael-type addition between azonaphthalenes and arylboronic acids for the construction of biaryl atropisomers was established using a novel BINOL-derived phosphoramidite as a chiral ligand. A broad range of atropisomeric biaryls were obtained with good efficiency, and the practicality of this approach was verified by versatile transformations toward axially chiral ligands, catalysts, and other functional atropisomers. This set of catalytic systems successfully inhibited the routine 1,2-addition and promoted the formation of an aryl-aryl chiral axis. Meanwhile, this strategy bypassed the use of an oxidant as well as the harsh conditions normally necessary for transition-metal-mediated arene C-H coupling with arylboronic acids as an arylation counterpart, offering a straightforward alternative to access optically active biaryls.

Synthesis of substituted helicenes by Ir-catalyzed annulative coupling of biarylcarboxylic acid chlorides with alkynes

A series of substituted [4] and [5]helicenes were synthesized in moderate to good yields by an Ir-catalyzed annulative coupling of biarylcarboxylic acid chlorides with internal alkynes, which involves facile C-H bond cleavage and decarbonylation. The double annulative coupling of 1, 1′:5′, 1″-ternaphthalene- 2, 2″-dicarboxylic acid dichloride with 4-octyne was also accomplished to give rise to an S-shaped double helicene. Unexpectedly, a π-extended benzofluoranthene-merged [5]- helicene was constructed through the annulative coupling and the successive C(aryl)-C(aryl) bond forming reaction when 1, 1′:4′, 1″-ternaphthalene-2, 2″-dicarboxylic acid dichloride was employed as the substrate. The crystal structure and the optical properties of the latter unique product were also investigated.

Asymmetric Suzuki-Miyaura cross-coupling of 1-bromo-2-naphthoates using the helically chiral polymer ligand PQXphos

A single-handed helical polymer ligand PQXphos afforded axially chiral biaryl esters with high enantioselectivities in asymmetric Suzuki-Miyaura cross-coupling. The use of naphthyl bromide bearing a 2,4-dimethyl-3-pentyl ester resulted in both high yields and high enantioselectivities. Either enantiomer could be synthesized selectively by using a single PQXphos through a solvent-dependent switch of the helical chirality. This journal is

Ortho-lithium/magnesium carboxylate-driven aromatic nucleophilic substitution reactions on unprotected naphthoic acids

Substitution of an ortho-fluoro or methoxy group in 1- and 2-naphthoic acids furnishing substituted naphthoic acids occurs in good to excellent yields upon reaction with alkyl/vinyl/aryl organolithium and Grignard reagents, in the absence of a metal catalyst without the need to protect the carboxyl (CO 2H) group. This novel nucleophilic aromatic substitution is presumed to proceed via a precoordination of the organometallic with the substrate, followed by an addition/elimination.

METHOD FOR PREPARING CHEMICAL COMPOUNDS OF INTEREST BY NUCLEOPHILIC AROMATIC SUBSTITUTION OF AROMATIC CARBOXYLIC ACID DERIVATIVES SUPPORTING AT LEAST ONE ELECTRO-ATTRACTIVE GROUP

Method for preparing carboxylic acid derivatives by aromatic nucleophilic substitution, in which a carboxylic acid derivative having a single carboxyl functional group, or one of the salts thereof, the carboxylic acid derivative having, in the ortho posit

Asymmetric construction of binaphthyl by the chiral diether-mediated conjugate addition of naphthyllithium to naphthalenecarboxylic acid 2,6-di-t-butyl-4-methoxyphenyl ester

Two ways for the synthesis of binaphthyl were examined based on a chiral ligand-mediated asymmetric conjugate addition of 1-naphthyllithium to naththalene-2-carboxylic acid 2,6-di-t-butyl-4-methoxyphenyl esters. The one pot method by conjugate addition-el

Asymmetric synthesis of helical poly(quinoxaline-2,3-diyl)s by palladium-mediated polymerization of 1,2-diisocyanobenzenes: Effective control of the screw-sense by a binaphthyl group at the chain-end

Aromatizing polymerization of 1,2-diisocyanobenzene derivatives was mediated by optically active organopalladium(II) complexes bearing 1,1'- binaphth-2-yl groups to give optically active poly(quinoxaline-2,3-diyl)s with varying screw-sense selectivities, which crucially depended upon the substituents on the binaphthyl groups. The most effective catalyst, which has 7'-methoxy-1,1'-binaphthyl group, induced the formation of a single screw- sense. Isolation and structural analyses (single-crystal X-ray diffraction and 1H NMR spectroscopy) of intermediary [oligo(quinoxalinyl)]palladium complexes revealed that the screw-sense selection in the polymerization may be decisively governed by the diastereomeric ratios of the (terquinoxalinyl)palladium(II) complex intermediate.

Facile Synthesis of 1,1'-Binaphthyl-2-carboxylates via Nucleophilic Aromatic Substitution of 1-Methoxy-2-naphthoic Esters by 1-Naphthyl Grignard Reagents

Grignard reagents formed from 1-bromonaphthalenes smoothly displaced the 1-methoxyl group of 1-methoxy-2-naphthoic esters to provide a facile route of 1,1'-binaphthyl-2-carboxylic acids in excellent yields; the reaction of (S)-1-phenylethyl esters caused

Practical Synthesis of 1,1'-Binaphtyl-2-carboxylic Acids via Side Chain Oxidation of 2-Methyl-1,1'-binaphtyls

Four 1,1'-binaphtyl-2-carboxylic acids were obtained in 38-53 percent isolated yield via three-stage oxidation of 2-methyl-1,1'-binaphtyls, that is, i) NBS-bromination to benzylic bromides, ii) treatment with sodium salt of 2-nitropropane to aldehydes, and iii) KMnO4-oxidation to carboxylic acids.