475278-17-2

Upstream product

• 15231-91-1 6-bromo-naphthalen-2-ol 
• 98-80-6 phenylboronic acid 
• 3900-46-7 N-(6-methoxynaphthalen-2-yl)acetamide 
• 3262-89-3 triphenylboroxine 
• 125363-65-7 2-acetoxy-6-hydroxynaphthalene 
• 59115-43-4 2-methoxy-6-phenylnaphthalene 
• 628-13-7 pyridine hydrochloride 
• 873973-58-1 N-(6-methoxy-[2]naphthyl)-N-nitroso-acetamide 
• 5111-65-9 2-Bromo-6-methoxynaphthalene 
• 412314-34-2 6-cyclohexyl-4,4a,5,6,7,8-hexahydro-3H-naphthalen-2-one 

Downstream Products

• 1196665-39-0 methyl 6'-phenyl-2,2'-dihydroxy-1,1'-binaphthyl-3-carboxylate 
• 1378043-06-1 diethyl (6-phenylnaphthalen-2-yl)phosphonate 
• 1378042-99-9 diphenyl(6-phenylnaphthalen-2-yl)phosphine oxide 
• 861046-41-5 6-phenylnaphthalen-2-amine 
• 1122065-34-2 6-phenylnaphthalen-2-yl pivalate 
• 1247758-32-2 2-phenyl-6-(p-tolyl)naphthalene 

Relevant academic research and scientific papers

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.

Dearomatizing [4+1] Spiroannulation of Naphthols: Discovery of Thermally Activated Delayed Fluorescent Materials

Disclosed here is a palladium-catalyzed direct [4+1] spiroannulation of ortho-C?H bonds of naphthols with cyclic diaryliodonium salts to construct spirofluorenyl naphthalenones (SFNP) under mild reaction conditions. This spiroannulation directly transforms the hydroxy group into a carbonyl group, and also tolerates reactive functional groups such as the halo groups, which provide an opportunity to rapidly assemble structurally new thermally activated delayed fluorescent (TADF) materials that feature a carbonyl group with an adjacent spirofluorenyl unit as the acceptor. As an illustrated example, the OLED device utilizing the assembled DMAC-SFNP as the host material exhibits a low turn-on voltage of 2.5 V and an ultra-high external quantum efficiency of 32.2 %. This work provides inspiration for structurally new TADF materials, and also displays the potential of C?H activation as a synthetic strategy for the innovation of optoelectronic materials.

Benzazole derivatives and organic electroluminescent device including the same

Provided is a benzazole derivative which effectively absorbs a high-energy external light source in the UV region and thus minimizes damage to organic materials in an organic electroluminescent device, thereby contributing to a substantial improvement in the service life of the organic electroluminescent device. An organic electroluminescent device according to the present invention comprises: a first electrode; a second electrode; at least one organic layer disposed between the first electrode and the second electrode; and a capping layer, wherein the organic layer or the capping layer comprises a benzazole derivative represented by chemical formula 1 according to the present invention.

Cobalt?NHC Catalyzed C(sp2)?C(sp3) and C(sp2)?C(sp2) Kumada Cross-Coupling of Aryl Tosylates with Alkyl and Aryl Grignard Reagents

The first cobalt-catalyzed cross-coupling of aryl tosylates with alkyl and aryl Grignard reagents is reported. The catalytic system uses CoF3 and NHCs (NHC=N-heterocyclic carbene) as ancillary ligands. The reaction proceeds via highly selective C?O bond functionalization, leading to the corresponding products in up to 98 % yield. The employment of alkyl Grignard reagents allows to achieve a rare C(sp2)?C(sp3) cross-coupling of C?O electrophiles, circumventing isomerization and β-hydride elimination problems. The use of aryl Grignards leads to the formation of biaryls. The C?O cross-coupling sets the stage for a sequential cross-coupling by exploiting the orthogonal selectivity of the catalytic system.

Enantioselective iron/bisquinolyldiamine ligand‐catalyzed oxidative coupling reaction of 2‐naphthols

An iron‐catalyzed asymmetric oxidative homo‐coupling of 2‐naphthols for the synthesis of 1,1′‐Bi‐2‐naphthol (BINOL) derivatives is reported. The coupling reaction provides enantioenriched BINOLs in good yields (up to 99%) and moderate enantioselectivities (up to 81:19 er) using an iron‐complex generated in situ from Fe(ClO4)2 and a bisquinolyldiamine ligand [(1R,2R)‐N1,N2‐di(quinolin‐8‐yl)cyclohexane‐1,2‐diamine, L1]. A number of ligands (L2–L8) and the analogs of L1, with various substituents and chiral backbones, were synthesized and examined in the oxidative coupling reactions.

SMALL MOLECULE INHIBITORS OF A PROTEIN COMPLEX

Compositions and methods for treating thrombosis, inflammation, and atherosclerosis by administration of a compound that binds to KRIT1 to inhibit binding with HEG1.

The Interrupted Pummerer Reaction in a Sulfoxide-Catalyzed Oxidative Coupling of 2-Naphthols

A benzothiophene S-oxide catalyst, generated in situ by sulfur oxidation with H2O2, mediates the oxidative coupling of 2-naphthols. Key to the catalytic process is the capture and inversion of reactivity of a 2-naphthol partner, using an interrupted Pummerer reaction of an unusual benzothiophene S-oxide, followed by subsequent coupling with a second partner. The new catalytic manifold has been showcased in the synthesis of the bioactive natural products, (±)-nigerone and (±)-isonigerone. Although Pummerer reactions are used widely, their application in catalysis is rare, and our approach represents a new catalytic manifold for metal-free C?C bond formation.

Iodine(III)-Mediated, Controlled Di- or Monoiodination of Phenols

An oxidative procedure for the electrophilic iodination of phenols was developed by using iodosylbenzene as a nontoxic iodine(III)-based oxidant and ammonium iodide as a cheap iodine atom source. A totally controlled monoiodination was achieved by buffering the reaction medium with K3PO4. This protocol proceeds with short reaction times, at mild temperatures, in an open flask, and generally with high yields. Gram-scale reactions, as well as the scope of this protocol, were explored with electron-rich and electron-poor phenols as well as heterocycles. Quantum chemistry calculations revealed PhII(OH)·NH3 to be the most plausible iodinating active species as a reactive "I+" synthon. In light of the relevance of the iodoarene moiety, we present herein a practical, efficient, and simple procedure with a broad functional group scope that allows access to the iodoarene core unit.

C -Glycosylation of Substituted β-Naphthols with Trichloroacetimidate Glycosyl Donors

Several glycosyl donors have been systematically investigated for C-glycosylation of substituted β-naphthols to delineate the effect of the substituents. Whereas glycosylations of the parent 2-naphthol are smoothly achievable, those of differently substituted 2-naphthols are cumbersome. Efficiency of the glycosylation depends on the nature of both the glycosyl donors and the substituents of the arene ring. Among various glycosyl donors, trichloroacetimidate glycosyl donors are found to be superior for glycosylation with substituted 2-naphthols.

Annulation of β-naphthols and 4-hydroxycoumarins with vinylsulfonium salts: Synthesis of dihydrofuran derivatives

A new synthetic approach to dihydrofuran derivatives via the annulation reaction of β-naphthols and 4-hydroxycoumarins with vinylsulfonium salts has been developed. A variety of dihydrofuran derivatives were prepared in moderate to good yields under mild conditions. The products could be readily transformed to the corresponding furans via the dehydrogenation with DDQ.