39070-97-8

Usage

Uses

Used in Chemical Industry:
(4-methoxyphenyl)(naphthalen-2-yl)methanone is used as an intermediate in the synthesis of other organic compounds for various applications.
Used in Pharmaceutical Industry:
(4-methoxyphenyl)(naphthalen-2-yl)methanone is used as a potential pharmacological and biological agent due to its potential activities.
It is important to handle and use (4-methoxyphenyl)(naphthalen-2-yl)methanone with caution and according to proper safety protocols.

Upstream product

• 100-66-3 methoxybenzene 
• 2243-83-6 2-naphthaloyl chloride 
• 580-13-2 2-bromonaphthalene 
• 100-07-2 4-methoxy-benzoyl chloride 
• 21473-01-8 2-naphthalenylmagnesium bromide 
• 123-11-5 4-methoxy-benzaldehyde 
• 201230-82-2 carbon monoxide 
• 5720-07-0 4-methoxyphenylboronic acid 
• 450-58-8 2-naphthyldiazonium tetrafluoroborate 
• 33397-21-6 tris(4-methoxyphenyl)bismuth 
• 123871-50-1 2-(p-methoxystyryl)naphthalene 
• 32316-92-0 naphthalene-2-boronic acid 
• 874-90-8 4-methoxybenzonitrile 
• 93296-09-4 4-methoxyphenylzinc chloride 

Downstream Products

• 102599-41-7 1-(4-methoxy-phenyl)-1-[2]naphthyl-pent-2-yne-1,5-diol 
• 859181-48-9 1,2-bis-(4-methoxy-phenyl)-1,2-di-[2]naphthyl-ethane-1,2-diol 
• 32891-91-1 2-(4-methoxy-benzyl)-naphthalene 
• 39070-82-1 (3,5-Dibromo-4-hydroxy-phenyl)-naphthalen-2-yl-methanone 
• 39070-83-2 (4-Hydroxy-3,5-diiodo-phenyl)-naphthalen-2-yl-methanone 
• 87643-54-7 p-methoxyphenyl 2-naphthyl thioketone 
• 39070-90-1 (4-hydroxyphenyl)(naphthalen-2-yl)methanone 

Relevant academic research and scientific papers

Synthesis of biaryl ketones by arylation of Weinreb amides with functionalized Grignard reagents under thermodynamic controlvs.kinetic control ofN,N-Boc2-amides

A highly efficient method for chemoselective synthesis of biaryl ketones by arylation of Weinreb amides (N-methoxy-N-methylamides) with functionalized Grignard reagents is reported. This protocol offers rapid entry to functionalized biaryl ketones after Mg/halide exchange with i-PrMgCl·LiCl under operationally-simple and practical reaction conditions. The scope of the method is highlighted in >40 examples, including bioactive compounds and pharmaceutical derivatives. Collectively, this transition-metal-free approach offers a major advantage over the recently established cross-coupling of amides by oxidative addition of N-C(O) bonds. Considering the utility of amide acylation reactions in modern synthesis, we expect that this method will be of broad interest.

Kinetically Controlled, Highly Chemoselective Acylation of Functionalized Grignard Reagents with Amides by N?C Cleavage

The direct transition-metal-free acylation of amides with functionalized Grignard reagents by highly chemoselective N?C cleavage under kinetic control has been accomplished. The method offers rapid and convergent access to functionalized biaryl ketones through transient tetrahedral intermediates. The direct access to functionalized Grignard reagents by in situ halogen–magnesium exchange promoted by the versatile turbo-Grignard reagent (iPrMgCl?LiCl) permits excellent substrate scope with respect to both the amide and Grignard coupling partners. These reactions enable facile, operationally simple and chemoselective access to tetrahedral intermediates from amides under significantly milder conditions than chelation-controlled intermediates. This novel direct two-component coupling sets the stage for using amides as acylating reagents in an alternative paradigm to the metal-chelated approach, acyl metals and Weinreb amides.

COMPOUND FOR ORGANIC SYNTHETIC REACTION

PROBLEM TO BE SOLVED: To provide a compound for organic synthetic reaction capable of reducing unnecessary reaction byproduct and generating a targeted chemical reaction effectively, even when a base compound sensitive to basicity is used. SOLUTION: There is provided a compound for organic synthetic reaction which is used for a coupling reaction or an addition reaction forming a bond between carbon-carbon, and is a compound represented by the structure formula (1) or a salt thereof. In the formula, (A) represents an oxygen atom or a nitrogen atom, R1 represents a substituent containing one or more carbon atom, R2 represents a substituent containing one or more carbon atom, hydrogen or halogen, and R1 and R2 may be the same or different each other. SELECTED DRAWING: Figure 2 COPYRIGHT: (C)2019,JPOandINPIT

Rapidly Activating Pd-Precatalyst for Suzuki-Miyaura and Buchwald-Hartwig Couplings of Aryl Esters

Esters are valuable electrophiles for cross-coupling due to their ubiquity and ease of synthesis. However, harsh conditions are traditionally required for the effective cross-coupling of ester substrates. Utilizing a recently discovered precatalyst, Pd-catalyzed Suzuki-Miyaura and Buchwald-Hartwig reactions involving cleavage of the C(acyl)-O bond of aryl esters that proceed under mild conditions are reported. The Pd(II) precatalyst is highly active because it is reduced to the Pd(0) active species more rapidly than previous precatalysts.

N-Acylsuccinimides: Efficient acylative coupling reagents in palladium-catalyzed Suzuki coupling via C–N cleavage

An acylative Suzuki coupling of activated amides with aryl boronic acids has been reported via palladium-catalyzed C–N bond cleavage. This protocol demonstrate amides can be activated by an atom-economic and cheap succinimide, which can be efficiently utilized to synthesize broad array of diaryl ketones in moderate to good yields.

The second aryl ketone compounds

The invention provides a synthetic method for diaryl ketone compounds. The method comprises the following steps: adding ester derivatives of raw material diaryl methanol, DDQ and water into an organic solvent, carrying out stirring, then carrying out heating to 110 to 140 DEG C and carrying out reaction for 0.5 to 12 h, and subjecting obtained reaction liquid to after-treatment so as to obtain the diaryl ketone compounds, wherein the ester derivatives of the raw material diaryl methanol have a structural formula as shown in a formula (V), (VI), (VII) or (VIII), and one-to-one correspondingly obtained products have the structural formula as shown in the formula (I), (II), (III) or (IV). The synthetic method for the diaryl ketone compounds provided by the invention has the advantages of simple, convenient and safe operation, mild reaction conditions and high product selectivity.

Ni-Catalyzed cross-coupling reactions of N-acylpyrrole-type amides with organoboron reagents

The catalytic conversion of amides to ketones is highly desirable yet challenging in organic synthesis. We herein report the first Ni/bis-NHC-catalyzed cross-coupling of N-acylpyrrole-type amides with arylboronic esters to obtain diarylketones. This method is facilitated by a new chelating bis-NHC ligand. The reaction tolerates diverse functional groups on both arylamide and arylboronic ester partners including sensitive ester and ketone groups.

Palladium Catalyzed Carbonylative Coupling for Synthesis of Arylketones and Arylesters Using Chloroform as the Carbon Monoxide Source

We describe a modular, palladium catalyzed synthesis of aryl(hetero)aryl benzophenones and aryl benzoates from aryl(hetero)aryl halides using CHCl3 as the carbonyl source in the presence of KOH. The reaction occurs in tandem through an initial carbonylation to generate an aroyl halide, which undergoes coupling with arylboronic acids, bornonates, and phenols. Direct carbonylative coupling of indoles at the third position has also been accomplished under slightly modified reaction conditions by in situ activation of the C-H bond. Notably, CHCl3 is a convenient and safe alternation of CO gas, provides milder reaction conditions with high functional group tolerance, and gives the products in moderate to good yields.

Ni-Catalyzed Reductive Cross-Coupling of Amides with Aryl Iodide Electrophiles via C-N Bond Activation

A Ni-catalyzed reductive cross-coupling reaction between two electrophiles, amides and aryl iodides, has been developed. This work is the first example using amide as an electrophile to couple with another electrophile, instead of using highly basic and pyrophoric nucleophiles. Furthermore, the Ni catalyst chemoselectively inserting the C-N bond of amide triggered the reductive cross-coupling reaction, which solves the problem that the Ni catalyst preferentially inserts the more reactive C-I bond to form a self-coupling product.

Nickel-catalyzed diaryl ketone synthesis by N-C cleavage: Direct negishi cross-coupling of primary amides by site-selective N,N-Di-boc activation

A general Negishi acylation of primary amides enabled by a combination of site-selective N,N-di-Boc activation and nickel catalysis is reported for the first time. The reaction is promoted by a bench-stable, inexpensive Ni catalyst. The reaction shows excellent functional group compatibility, affording functionalized diaryl ketones by selective N-C cleavage. Most notably, this protocol represents the first amide cross-coupling by direct metal insertion of simple and readily available primary amides. The overall strategy by N,N-di-Boc activation/metal insertion is suitable for a broad range of coupling protocols via acylmetals. Mechanistic experiments suggest high reactivity of N,N-di-Boc activated 1° amides in direct amide C-N cross-couplings.