93327-64-1

Upstream product

• 491-38-3 1-benzopyran-4(4H)-one 
• 2471-91-2 1,3-dihydrobenzo[c]thiophene-2,2-dioxide 
• 17422-74-1 3-Formylchromone 
• 32316-92-0 naphthalene-2-boronic acid 
• 90-02-8 salicylaldehyde 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 93-09-4 naphthalene-2-carboxylate 
• 91-20-3 naphthalene 
• 118-55-8 phenyl Salicylate 
• 82408-29-5 phenyl naphthalene-2-carboxylate 
• 703-55-9 1-naphthylmagnesiumbromide 
• 93-11-8 2-Naphthalenesulfonyl chloride 
• 69-72-7 salicylic acid 
• 115237-37-1 3-[(1E)-2-phenylethenyl]-4H-1-benzopyran-4-one 

Downstream Products

• 1334247-44-7 (S)-2-(amino(naphthalen-2-yl)methyl)phenol 
• 1245607-13-9 1-(2-naphthyl)-1-(2-hydroxyphenyl)methylenimine 
• 1309688-77-4 C₃₂H₁₆F₅NO₂ 
• 1309688-87-6 C₂₅H₁₇N 
• 68299-60-5 2-((naphthalen-2-yl)methyl)phenol 

Relevant academic research and scientific papers

Frustrated excited state intramolecular proton transfer (ESIPT) in 10-hydroxy-11H-benzo[b]fluoren-11-one: Synthesis and photophysics

A new hydroxybenzofluorenone has been designed and synthesised in order to investigate the origin of excited state intramolecular proton transfer reactions in this familiy of compounds. 10-Hydroxy-11H-benzo [b]fluoren-11-one (10-HHBF) does not show dual f

Aerobic Copper-Catalyzed Salicylaldehydic Cformyl?H Arylations with Arylboronic Acids

We report a challenging copper-catalyzed Cformyl?H arylation of salicylaldehydes with arylboronic acids that involves unique salicylaldehydic copper species that differ from reported salicylaldehydic rhodacycles and palladacycles. This protocol has high chemoselectivity for the Cformyl?H bond compared to the phenolic O?H bond involving copper catalysis under high reaction temperatures. This approach is compatible with a wide range of salicylaldehyde and arylboronic acid substrates, including estrone and carbazole derivatives, which leads to the corresponding arylation products. Mechanistic studies show that the 2-hydroxy group of the salicylaldehyde substrate triggers the formation of salicylaldehydic copper complexes through a CuI/CuII/CuIII catalytic cycle.

Ruthenium-Catalyzed Direct Asymmetric Reductive Amination of Diaryl and Sterically Hindered Ketones with Ammonium Salts and H2

A Ru-catalyzed direct asymmetric reductive amination of ortho-OH-substituted diaryl and sterically hindered ketones with ammonium salts is reported. This method represents a straightforward route toward the synthesis of synthetically useful chiral primary diarylmethylamines and sterically hindered benzylamines (up to 97 % yield, 93–>99 % ee). Elaborations of the chiral amine products into bioactive compounds and a chiral ligand were demonstrated through manipulation of the removable and convertible -OH group.

Deoxygenative Arylation of Carboxylic Acids by Aryl Migration

An unprecedented deoxygenative arylation of aromatic carboxylic acids has been achieved, allowing the construction of an enhanced library of unsymmetrical diaryl ketones. The synergistic photoredox catalysis and phosphoranyl radical chemistry allows for precise cleavage of a stronger C?O bond and formation of a weaker C?C bond by 1,5-aryl migration under mild reaction conditions. This new protocol is independent of substrate redox-potential, electronic, and substituent effects. It affords a general and promising access to 60 examples of synthetically versatile o-amino and o-hydroxy diaryl ketones under redox-neutral conditions. Furthermore, it also brings one concise route to the total synthesis of quinolone alkaloid, (±)-yaequinolone A2, and a viridicatin derivative in satisfying yields.

Integrating Metal-Catalyzed C-H and C-O Functionalization to Achieve Sterically Controlled Regioselectivity in Arene Acylation

One major goal of organometallic chemists is the direct functionalization of the bonds most recurrent in organic molecules: C-H, C-C, C-O, and C-N. An even grander challenge is C-C bond formation when both precursors are of this category. Parallel to this is the synthetic goal of achieving reaction selectivity that contrasts with conventional methods. Electrophilic aromatic substitution (EAS) via Friedel-Crafts acylation is the most renowned method for the synthesis of aryl ketones, a common structural motif of many pharmaceuticals, agrochemicals, fragrances, dyes, and other commodity chemicals. However, an EAS synthetic strategy is only effective if the desired site for acylation is in accordance with the electronic-controlled regioselectivity of the reaction. Herein we report steric-controlled regioselective arene acylation with salicylate esters via iridium catalysis to access distinctly substituted benzophenones. Experimental and computational data indicate a unique reaction mechanism that integrates C-O activation and C-H activation with a single iridium catalyst without an exogenous oxidant or base. We disclose an extensive exploration of the synthetic scope of both the arene and the ester components, culminating in the concise synthesis of the potent anticancer agent hydroxyphenstatin.

Palladium-catalyzed direct mono -aroylation of O -arylmethyl and aryl-substituted acetoxime ethers

An efficient palladium-catalyzed ortho-aroylation of O-arylmethyl and aryl-substituted acetoxime ethers has been developed; this method has high mono-site selectivity and does not require exogenous ligands. Under the direction of a simple exo-acetoxime auxiliary, a broad scope of masked arylmethyl alcohols and phenols as well as various aromatic aldehydes are compatible with this transformation, which probably follows a mechanistic pathway involving a six- or five-membered exo-cyclopalladated intermediate. The strategy can be expediently adopted to prepare synthetically valuable 1H-benzo[d][1,2]oxazines and benzo[d]isoxazoles. The directing group can be easily removed from the products to afford the functionalized diaryl ketones.

Synthesis of Benzoaryl-5-yl(2-hydroxyphenyl)methanones via Photoinduced Rearrangement of (E)-3-Arylvinyl-4H-chromen-4-ones

A concise and efficient photoinduced rearrangement of (E)-3-arylvinyl-4H-chromen-4-ones for the synthesis of benzoaryl-5-yl(2-hydroxyphenyl)methanones is described. Benzoaryl-5-yl-(2-hydroxyphenyl)methanones were obtained in 77-95% yields via the irradiation of (E)-3-arylvinyl-chromones in the 95% EtOH with a high-pressure mercury lamp at room temperature under Ar atmosphere. The reported method provides a novel procedure for the synthesis of α,α′-diaryl ketone derivatives without addition of any transition metals and oxidants or other additives. A plausible mechanism was proposed, and the rearrangement product was characterized by NMR, HRMS, and X-ray.

Rh(III)-catalyzed aldehyde C-H bond functionalization of salicylaldehydes with arylboronic acids

A Rh(III)-catalyzed aldehyde C-H bond functionalization of salicylaldehydes with arylboronic acids has been developed, with features of mild reaction condition and high efficiency. Furthermore, the functionalized 2-hydroxybenzophenone could be subject to divergent synthesis of heterocycles.

Intermolecular C-O addition of carboxylic acids to arynes: Synthesis of o-hydroxyaryl ketones, xanthones, 4-chromanones, and flavones

An efficient and simple route to biologically and pharmaceutically important o-hydroxyaryl ketones, xanthones, 4-chromanones, and flavones has been developed utilizing readily available carboxylic acids and commercially available o-(trimethylsilyl)aryl tr

Direct C-H bond arylation of 2-hydroxybenzaldehydes with arylboronic acids via ligand-free palladium catalysis

A mild and efficient ligand-free palladium-catalyzed direct C-H bond arylation reaction was developed to afford 2-hydroxybenzophenones in good to excellent yields from easily available 2-hydroxybenzaldehydes and arylboronic acids. The given reaction provided one of the easiest pathways for accessing 2-hydroxybenzophenones, and a variety of functional groups could be tolerated in this process.