93845-81-9

Upstream product

• 201230-82-2 carbon monoxide 
• 696-62-8 para-iodoanisole 
• 693-02-7 hex-1-yne 
• 3844-94-8 1-(trimethylsilyl)-1-hexyne 
• 100-07-2 4-methoxy-benzoyl chloride 
• 115085-23-9 1-(4-methoxyphenyl)hept-2-yn-1-ol 
• 18414-58-9 diphenylmethylsilanecarboxylic acid 
• 132353-25-4 2-(4-methoxybenzoyloxy)-4,6-dimethoxy-1,3,5-triazine 
• 100-09-4 4-methoxybenzoic acid 
• 1159987-54-8 tri(hexyn-1-yl)indium 
• 123-11-5 4-methoxy-benzaldehyde 
• 105-13-5 4-Methoxybenzyl alcohol 
• 35864-20-1 1-hexynyltributyltin 
• 5720-07-0 4-methoxyphenylboronic acid 

Downstream Products

• 118083-67-3 (2E,4E)-1-(4-Methoxy-phenyl)-hepta-2,4-dien-1-one 
• 1137261-90-5 1-(4-methoxyphenyl)-1,3-heptanedione 

Relevant academic research and scientific papers

Bifunctional phosphine ligand-enabled gold-catalyzed direct cycloisomerization of alkynyl ketones to 2,5-disubstituted furans

An efficient synthesis of 2,5-disubstituted furans directly from alkynyl ketones has been developed via tandem gold(i)-catalyzed isomerization of alkynyl ketones to allenyl ketones and cycloisomerization. The key to the success of this chemistry is the use of a biphenyl-2-ylphosphine ligand featuring a critical remote tertiary amino group.

Copper-catalyzed method for preparing aldehyde or ketone compound by oxidizing alcohol with oxygen as oxidizing agent and application

The invention discloses a copper-catalyzed method for preparing an aldehyde or ketone compound by oxidizing alcohol with oxygen as an oxidizing agent. Reaction is performed in an organic solvent for 4-48 hours at room temperature by using copper salt and nitroxide free radicals as catalysts and oxygen or air as an oxidizing agent to efficiently oxidize an alcohol compound into the corresponding aldehyde or ketone compound. The method is simple to operate, free of chlorides corrosive to equipment, available in raw materials and reagents, mild in reaction conditions, wide in substrate universality, good in functional group compatibility, convenient in separation and purification, environmentally friendly in the whole process and free of pollution, and is a method suitable for industrial production.

Copper-Catalyzed Aminoboration from Hydrazones to Generate Borylated Pyrazoles

Herein we report an aminoboration reaction that employs inexpensive, Earth-abundant, and commercially available Cu(OTf)2 as an effective catalyst in the direct addition of B-N σ bonds to C-C π bonds, generating borylated pyrazoles, which are us

Carbonylative Sonogashira Coupling of Aryl Iodides with Terminal Alkynes Catalyzed by Palladium Nanoparticles

A convenient and efficient method for the synthesis of α,β-alkynyl ketones from the three-component coupling of aryl iodides, terminal alkynes, and carbon monoxide (carbonylative Sonogashira coupling reaction) is successfully developed. The carbonylative Sonogashira coupling reaction proceeded smoothly under mild conditions in the presence of palladium nanoparticles to produce the corresponding α,β-alkynyl ketones in good to excellent yields.

Gem-Digold Acetylide Complexes for Catalytic Intermolecular [4 + 2] Cycloaddition: Having Two Gold Centers Is Better for Asymmetric Catalysis

Gold(I)-catalyzed highly enantioselective intermolecular [4 + 2] cycloaddition is shown with ynones and cyclohexadiene. Various bicyclo[2.2.2]octadiene derivatives are produced in high yields (up to 99%) with good enantioselectivity (up to 96% ee). Key to the success is generation of the gem-digold terminal alkyne as a catalytic on-cycle species. As proof of the gem-digold catalysis, a positive nonlinear effect is clarified between the ee's of the ligand and the cycloadduct.

Nano CoCuFe2O4 catalyzed coupling reaction of acid chlorides with terminal alkynes: A powerful toolbox for palladium-free ynone synthesis

The present work describes the application of nano CoCuFe2O4 toward the coupling reaction of acyl chlorides with terminal alkynes. By this catalytic system, ynone derivatives were formed in high yields via a palladium-free strategy.

A phosphine-free, heterogeneous palladium-catalyzed atom-efficient carbonylative cross-coupling of triorganoindiums with aryl halides leading to unsymmetrical ketones

The first phosphine-free heterogeneous palladium-catalyzed carbonylative cross-coupling of aryl halides with triorganoindiums has been developed that proceeds smoothly under 1 or 2.5 atm of carbon monoxide in THF at 68 °C and provides a general and powerful tool for the synthesis of various valuable unsymmetrical ketones with high atom-economy, good yield, and recyclability of the catalyst. Our system not only avoids the use of phosphine ligands, but also solves the basic problem of palladium catalyst recovery and reuse.

Oxyboration with and without a Catalyst: Borylated Isoxazoles via B-O-Bond Addition

Herein we report an oxyboration reaction with activated substrates that employs B-O σ bond additions to C-C π bonds to form borylated isoxazoles, which are potential building blocks for drug discovery. Although this reaction can be effectively catalyzed by gold, it is the first example of uncatalyzed oxyboration of C-C π bonds by B-O σ bonds-and only the second example that is catalyzed. This oxyboration reaction is tolerant of groups incompatible with alternative lithiation/borylation and palladium-catalyzed C-H activation/borylation technologies for the synthesis of borylated isoxazoles.

A highly efficient heterogeneous palladium-catalyzed cascade three-component reaction of acid chlorides, terminal alkynes and hydrazines leading to pyrazoles

In the presence of 0.5 mol% of 3-(2-aminoethylamino)propyl-functionalized MCM-41-immobilized palladium(II) complex [MCM-41-2N-Pd(OAc)2] and 1.0 mol% of CuI, acid chlorides were coupled with terminal alkynes in Et3N at 50 °C to give α,β-unsaturated ynones, which were converted in situ into pyrazoles by the cycloaddition of hydrazines at room temperature with acetonitrile as cosolvent. The cascade reactions generated a variety of pyrazole derivatives in moderate to good yields, and this heterogeneous palladium catalyst exhibited higher catalytic activity than PdCl2(PPh3)2 and could be recovered and reused for at least 10 consecutive trials without any decreases in activity.

Consecutive three- and four-component coupling-Bagley-Bohlmann-Rahtz syntheses of tri- and tetrasubstituted pyridines

The concatenation of the modified Sonogashira alkynone synthesis and the Bagley-Bohlmann-Rahtz pyridine synthesis gives novel consecutive three- and four-component coupling-Bagley-Bohlmann-Rahtz (cBBR) syntheses of tri- and tetrasubstituted pyridines in a one-pot fashion. With these processes 15 differently substituted 3-ethoxycarbonyl 2-methylpyridines can be readily obtained in modest to moderate yields.