729-17-9

Usage

Uses

Used in Organic Synthesis:
METHYL 4'-METHOXYBIPHENYL-4-CARBOXYLATE is used as a reagent for the synthesis of functionalized diaryl ketones. It plays a crucial role in nickel/palladium-catalyzed carbonylative cross-coupling reactions, which are essential for the production of a wide range of organic compounds with potential applications in various industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, METHYL 4'-METHOXYBIPHENYL-4-CARBOXYLATE is used as a key intermediate in the synthesis of various drug molecules. Its ability to participate in carbonylative cross-coupling reactions enables the creation of complex molecular structures that can exhibit therapeutic properties.
Used in Chemical Research:
METHYL 4'-METHOXYBIPHENYL-4-CARBOXYLATE is also utilized in chemical research for the development and optimization of new synthetic methods and reaction conditions. Its involvement in carbonylative cross-coupling reactions provides a platform for researchers to explore novel approaches to organic synthesis and improve the efficiency and selectivity of these processes.

Upstream product

• 124-41-4 sodium methylate 
• 733-53-9 p-methoxyphenyl(phenyl)iodonium tetrafluoroborate 
• 109-72-8 n-butyllithium 
• 161497-18-3 methyl 4-(methanesulfonyloxy)benzoate 
• 215877-38-6 4,5-dimethyl-2-(4-methoxyphenyl)-1,3,2-dioxaborolane 
• 619-44-3 methyl 4-iodobenzoate 
• 5720-07-0 4-methoxyphenylboronic acid 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 1126-46-1 Methyl 4-chlorobenzoate 
• 696-62-8 para-iodoanisole 
• 99768-12-4 4-methoxycarbonylphenylboronic acid 
• 7377-26-6 4-Methoxycarbonylbenzoyl chloride 
• 6725-72-0 4-methoxycarbonylbenzoic acid phenyl ester 
• 1679-64-7 Monomethyl terephthalate 

Downstream Products

• 20854-64-2 6--indanol-(1) 
• 22490-64-8 6-(4-methoxyphenyl)-indan-1-one 
• 20854-67-5 6--2-oximino-indanon-(1) 
• 20902-20-9 6--cis-indandiol-(1,2) 
• 20902-20-9 6--trans-indandiol-(1,2) 
• 1632171-05-1 methyl 3'-acetyl-4'-hydroxy-[1,1'-biphenyl]-4-carboxylate 
• 1632171-09-5 methyl 4-(spiro[chromene-2,4'-piperidin]-6-yl)benzoate 
• 1632171-08-4 methyl 4-(spiro[chromane-2,4'-piperidin]-6-yl)benzoate 
• 1632171-12-0 (4-(spiro[chromane-2,4'-piperidin]-6-yl)phenyl)methanol 
• 1632171-11-9 C₂₁H₂₃NO₃*ClH 
• 1632171-06-2 tert-butyl 6-(4-(methoxycarbonyl)phenyl)-4-oxospiro[chromane-2,4'-piperidine]-1'-carboxylate 
• 1632171-07-3 tert-butyl 4-hydroxy-6-(4-(methoxycarbonyl)phenyl)spiro[chromane-2,4'-piperidine]-1'-carboxylate 

Relevant academic research and scientific papers

Bathocuproine-Enabled Nickel-Catalyzed Selective Ullmann Cross-Coupling of Two sp 2-Hybridized Organohalides

Cross-coupling reactions are essential for the synthesis of complex organic molecules. Here, we report a nickel-catalyzed Ullmann cross-coupling of two sp 2-hybridized organohalides, featuring high cross-selectivity when the two coupling partners are used in a 1:1 ratio. The high chemoselectivity is governed by the bathocuproine ligand. Moreover, the mild reductive reaction conditions allow that a wide range of functional groups are compatible in this Ullmann cross-coupling.

New Nickel-Based Catalytic System with Pincer Pyrrole-Functionalized N-Heterocyclic Carbene as Ligand for Suzuki-Miyaura Cross-Coupling Reactions

A new catalytic system with Ni(NO3)2·6H2O as the catalyst and a pincer pyrrole-functionalized N-heterocyclic carbene as the ligand was employed in the Suzuki-Miyaura cross-coupling reactions of aryl iodides with arylboronic acids. With 5 mol% catalyst, the catalytic reactions proceeded at 160 °C, giving coupling products in isolated yields of up to 94% in short reaction times (1-4 h). The system worked efficiently with aryl iodides bearing electron-donating or electron-withdrawing groups and arylboronic acids with electron-donating groups. Steric effects were observed for both aryl iodides and arylboronic acids. It is proposed that the reactions underwent a Ni(I)/Ni(III) catalytic cycle.

para-Selective arylation and alkenylation of monosubstituted arenes using thianthreneS-oxide as a transient mediator

Using thianthreneS-oxide (TTSO) as a transient mediator,para-arylation and alkenylation of mono-substituted arenes have been demonstratedviaapara-selective thianthrenation/Pd-catalyzed thio-Suzuki-Miyaura coupling sequence under mild conditions. This reaction features a broad substrate scope, and functional group and heterocycle tolerance. The versatility of this approach was further demonstrated by late-stage functionalization of complex bioactive scaffolds, and direct synthesis of some pharmaceuticals, including Tetriprofen, Ibuprofen, Bifonazole, and LJ570.

Preparation method of para-substituted aryl compound

The invention discloses a preparation method of a para-substituted aryl compound shown as a formula (I) which is described in the specfication. The preparation method is characterized by comprising the following step of: subjecting an aryl sulfonium salt shown as a formula (II) which is described in the specfication and boride to a coupling reaction in a solvent in an inert atmosphere under the action of alkali and a palladium catalyst to obtain the para-substituted aryl compound. According to the method, mono-substituted aromatic hydrocarbon is taken as a substrate, the aryl sulfonium salt isconstructed in situ, and the palladium catalyst catalyzes the aryl sulfonium salt constructed in situ to undergo the Suzuki-Miyaura coupling reaction, so a mono-substituted aromatic hydrocarbon para-arylation or alkenylation product is constructed quickly and efficiently. The method is mild in conditions, high in substrate universality and wide in tolerance of a heterocyclic coupling substrate.

Azole-based non-peptidomimetic plasmepsin inhibitors

The spread of drug-resistant malaria parasites urges the search for new antimalarial drugs. Malarial aspartic proteases – plasmepsins (Plms) – are differentially expressed in multiple stages of the Plasmodium parasite's lifecycle and are considered as attractive drug targets. We report the development of novel azole-based non-peptidomimetic plasmepsin inhibitors that have been designed by bioisosteric substitution of the amide moiety in the Actelion amino-piperazine inhibitors. The best triazole-based inhibitors show submicromolar potency toward Plm II, which is comparable to that of the parent Actelion compounds. The new inhibitors can be used as a starting point for the development of a resistance-free antimalarial drug targeting the non-digestive Plm IX or X, which are essential for the malaria parasite life cycle.

Base-free nickel-catalysed decarbonylative Suzuki–Miyaura coupling of acid fluorides

The Suzuki–Miyaura cross-coupling of organoboron nucleophiles with aryl halide electrophiles is one of the most widely used carbon–carbon bond-forming reactions in organic and medicinal chemistry1,2. A key challenge associated with these transformations is that they generally require the addition of an exogenous base, the role of which is to enable transmetallation between the organoboron nucleophile and the metal catalyst3. This requirement limits the substrate scope of the reaction because the added base promotes competitive decomposition of many organoboron substrates3–5. As such, considerable research has focused on strategies for mitigating base-mediated side reactions6–12. Previous efforts have primarily focused either on designing strategically masked organoboron reagents (to slow base-mediated decomposition)6–8 or on developing highly active palladium precatalysts (to accelerate cross-coupling relative to base-mediated decomposition pathways)10–12. An attractive alternative approach involves identifying combinations of catalyst and electrophile that enable Suzuki–Miyaura-type reactions to proceed without an exogenous base12–14. Here we use this approach to develop a nickel-catalysed coupling of aryl boronic acids with acid fluorides15–17, which are formed in situ from readily available carboxylic acids18–22. This combination of catalyst and electrophile enables a mechanistic manifold in which a ‘transmetallation-active’ aryl nickel fluoride intermediate is generated directly in the catalytic cycle13,16. As such, this transformation does not require an exogenous base and is applicable to a wide range of base-sensitive boronic acids and biologically active carboxylic acids.

A crosslinked bis(amino)-containing polymer as a remarkable support for heterogeneous palladium-catalyzed Suzuki-Miyaura reaction

Through the substitution reaction of hexachlorocyclotriphosphazene (HCCP) and 4,4′-diaminobiphenyl (DABP), a crosslinked polymer HCCP-DABP was synthesized by a conventional and convenient route. Owing to the strong coordination ability of pincer-type bis(amino) scaffold in the matrix, the polymer was successfully used as a support to form stable palladium catalyst complex Pd/HCCP-DABP. The palladium catalyst showed excellent reactivity in Suzuki-Miyaura cross-coupling reaction. In addition, the catalyst can be readily recovered and reused for further transformations at least 10 times without significant decrease in catalytic activity.

SUBSTITUTED AMINOALKYLAZOLES AS MALARIAL ASPARTIC PROTEASE INHIBITORS

The present invention relates to novel aminoalkylazoles acting as inhibitors of malarial protease plasmepsin II. These can be used as medicines or as constituent of medicines for the treatment of malaria infection.

Tackling poison and leach: Catalysis by dangling thiol-palladium functions within a porous metal-organic solid

Self-standing thiol (-SH) groups within a Zr(iv)-based metal-organic framework (MOF) anchor Pd(ii) atoms for catalytic applications: the spatial constraint prevents the thiol groups from sealing off/poisoning the Pd(ii) center, while the strong Pd-S bond precludes Pd leaching, enabling multiple cycles of heterogeneous catalysis to be executed. This journal is

Nickel-Catalyzed Decarbonylative Coupling of Aryl Esters and Arylboronic Acids

A variety of functionalized biaryls can be accessed by coupling aryl and heteroaryl esters with boronic acids in Suzuki-Miyaura-type decarbonylative cross-coupling catalyzed by an affordable catalyst system composed of Ni(cod)2 and PCy3. The methodology is tolerant of a variety of functional groups and presents an attractive alternative to the use of palladium catalysis currently used in industry to acquire such bis(hetero)aryls, but also reveals challenges associated with nickel catalysis of esters in cross-coupling chemistry.