15982-64-6

Upstream product

• 100-66-3 methoxybenzene 
• 543-20-4 succinoyl dichloride 
• 2632-13-5 2-Bromo-4'-methoxyacetophenone 
• 2881-83-6 ethyl 4-methoxybenzoylacetate 
• 2196-99-8 2-chloro-1-(4-methoxyphenyl)ethanone 
• 75-15-0 carbon disulfide 
• 7446-70-0 aluminium trichloride 
• 5535-48-8 PVS 
• 123-11-5 4-methoxy-benzaldehyde 
• 27918-37-2 1-(4-methoxyphenyl)-2-(phenylsulfonyl)ethanone 
• 15331-49-4 trans-1,2-di(4-methoxybenzoyl)ethylene 
• 93624-01-2 O-ethyl S-2-(4-methoxyphenyl)-2-oxoethyl carbonodithioate 
• 201230-82-2 carbon monoxide 
• 696-62-8 para-iodoanisole 

Downstream Products

• 94762-50-2 2,5-bis-(4-methoxy-phenyl)-hexane-2,5-diol 
• 99872-35-2 2,5-Bis-(4-methoxy-phenyl)-2,5-dimethyl-tetrahydro-furan 
• 104891-45-4 1-methyl-2,5-bis(4-methoxyphenyl)pyrrole 
• 52498-16-5 1,4-bis-(4-methoxy-phenyl)-butane-1,4-diol 
• 97595-21-6 2,5-bis-(4-hydroxyphenyl)thiophene 
• 1014982-30-9 C₂₀H₁₉NO₄ 
• 52498-15-4 trans-1,2-bis(4-methoxyphenyl)cyclobutane 
• 52498-14-3 cis-1,2-bis(4-methoxyphenyl)cyclobutane 
• 52498-17-6 1,4-Bis-(p-anisyl)-1,4-dichlor-butan 
• 52498-18-7 1,2-bis(4-methoxyphenyl)cyclobut-1-ene 
• 97115-97-4 3,6-Bis-(4-methoxy-phenyl)-octadien-(3,5) 
• 854458-75-6 1,4-bis-(2-methoxy-phenyl)-1,4-bis-(4-methoxy-phenyl)-buta-1,3-diene 
• 54655-89-9 1,1,4,4-tetrakis(4-methoxyphenyl)butadiene 

Relevant academic research and scientific papers

Electrochemical reactivity of S-phenacyl-O-ethyl-xanthates in hydroalcoholic (MeOH/H2O 4:1) and anhydrous acetonitrile media

The electrochemical behavior of a series of S-phenacyl-O-ethyl-xanthates (O-ethyl-dithiocarbonate acetophenone derivatives) in hydroalcoholic (MeOH/H2O 4:1) and anhydrous media (ACN/TBAPF6) using carbon electrodes was studied. Cyclic voltammetry showed in hydroalcoholic media only two cathodic waves, whereas in ACN one anodic and two cathodic waves were present. The first cathodic wave corresponded to the reduction of the phenylketone group, whereas the first anodic was attributed to the xanthate unit. Macroelectrolysis on graphite and vitreous carbon at anodic and cathodic potentials, let us to explore the synthetic potential of this electrochemical reactions. With some compounds in hydroalcoholic media and using carbon electrodes, polymeric material was deposited on the electrode impeding the reaction; this deposit was characterized by AFM and SEM-EDS. The electroreduction on Ti electrode overcome this problem and gave the corresponding acetophenones (>95%). On the other hand, in ACN, small quantities of the dimeric 1,4-dicarbonyl compounds X-PhCOCH2CH2COPh-X (7–15%), as well as the corresponding acetophenones (ca. 50%) were isolated. Oxidation macroelectrolysis showed a very complicated transformation without synthetic value. The reaction mechanism for the reduction and the homolytic dissociation into the phenacyl radical was supported by DFT calculations.

Copper(I)/DDQ-Mediated Double-Dehydrogenative Diels-Alder Reaction of Aryl Butenes with 1,4-Diketones and Indolones

A copper(I)/DDQ-mediated double-dehydrogenative Diels-Alder (DDDA) reaction of simple butenes with 1,4-diketones and indolones has been established for the first time. This strategy is based on a tandem double-dehydrogenation/Diels-Alder reaction from nonprefunctionalized starting materials, in which both a diene and dienophile were in situ generated via activation of fourfold inert C(sp3)-H bonds in one catalytic system.

Lead-Halide Perovskites for Photocatalytic α-Alkylation of Aldehydes

Cost-effective and efficient photocatalysis are highly desirable in chemical synthesis. Here we demonstrate that readily prepared suspensions of APbBr3 (A = Cs or methylammonium (MA)) type perovskite colloids (ca. 2-100 nm) can selectively photocatalyze carbon-carbon bond formation reactions, i.e., α-alkylations. Specifically, we demonstrate α-alkylation of aldehydes with a turnover number (TON) of over 52,000 under visible light illumination. Hybrid organic/inorganic perovskites are revolutionizing photovoltaic research and are now impacting other research fields, but their exploration in organic synthesis is rare. Our low-cost, easy-to-process, highly efficient and bandedge-tunable perovskite photocatalyst is expected to bring new insights in chemical synthesis.

Synthesis of 2,2,5-Trisubstituted 2 H-Pyrroles and 2,3,5-Trisubstituted 1 H-Pyrroles by Ligand-Controlled Site-Selective Dearomative C2-Arylation and Direct C3-Arylation

Palladium-catalyzed site-selective dearomative C2-arylation of 2,5-diaryl-1H-pyrroles with aryl chlorides was accomplished, and a series of 2,2,5-triaryl-2H-pyrroles were synthesized. In addition, the site selectivity of the reaction was switched by simply changing the ligand, and the direct C3-arylated 2,3,5-triaryl-1H-pyrroles were prepared. The obtained 2,2,5-triaryl-2H-pyrroles could be further transformed into 2,2,5,5-tetraarylpyrrolidines.

One-Pot Synthesis of O-Heterocycles or Aryl Ketones Using an InCl3/Et3SiH System by Switching the Solvent

An efficient one-pot synthesis of O-heterocycles or aryl ketones has been achieved using Et3SiH in the presence of InCl3 via a sequential ionic hydrogenation reaction by switching the solvent. This methodology can be used to construct C-O bonds and to prepare conjugate reduction products, including chromans, tetrahydrofurans, tetrahydropyrans, dihydroisobenzofurans, dihydrochalcones, and 1,4-diones in a facile manner. In addition, a novel plausible mechanism involving a conjugate reduction and a tandem reductive cyclization was verified by experimental investigations.

Synthesis of 1,4-Diketones via Titanium-Mediated Reductive Homocoupling of α-Haloketones

1,4-Diketones have been synthesized via a reductive homocoupling of α-haloketones. Addition of a Grignard reagent to titanium(IV) isopropoxide affords a low-valent titanium(III) intermediate that is believed to mediate a radical dimerization reaction. The

Development of a Palladium-Catalyzed Carbonylative Coupling Strategy to 1,4-Diketones

We report on a three-component palladium-catalyzed coupling strategy for accessing a wide range of 1,4-diketones, which represent important precursors to heterocycles. Our method relies on a carbonylative Heck reaction employing substituted allylic alcohols, aryl iodides, and carbon monoxide. The reaction conditions are mild and do not require high CO pressure, and a wide functional group tolerance is revealed, providing the desired 1,4-diketones in moderate to good yields. Furthermore, the methodology is adaptable to the selective installment of 13C-carbon isotopes at either one or both of the carbonyl positions.

Breaking bonds with electrons: Stepwise and concerted reductive cleavage of C-S, C-Se and Se-CN bonds in phenacylthiocyanates and phenacylselenocyanates

The mechanistic aspects of the electrochemical reduction of phenacylthio- and selenocyanates have been studied. With phenacylthiocyanates (1), a change in the reductive cleavage mechanism is observed as a function of the substituent on the phenyl ring. While a stepwise mechanism involving the intermediacy of a radical anion is followed for substrates bearing a strong electron withdrawing group, such as cyano and nitro substituent (1d, 1e), and a concerted mechanism is favoured for compounds bearing an electron-donating or no substituent on the phenyl ring (1a-c). A regioselective bond cleavage leads to the fragmentation of the CH2-S bond with all compounds 1a-e, further yielding the corresponding 1,4-diketone (3) as products. Contrastingly, with phenacylselenocyanates (2), two different reductive cleavages occur involving the breaking of both the CH2-Se and Se-CN bonds. Several products are obtained, all coming from nucleophilic attack at the α (phenacyl) carbon or the selenium atom.

Flexible stereoselective functionalizations of ketones through umpolung with hypervalent iodine reagents

The functionalization of carbonyl compounds in the α-position has gathered much attention as a synthetic route because of the wide biological importance of such products. Through polarity reversal, or "umpolung", we show here that typical nucleophiles, such as oxygen, nitrogen, and even carbon nucleophiles, can be used for addition reactions after tethering them to enol ethers. Our findings allow novel retrosynthetic planning and rapid assembly of structures previously accessible only by multistep sequences. A Nu approach: An efficient α-functionalization of ketones with a range of simple and useful nucleophiles is possible by using hypervalent iodine reagents (see scheme; Nu′ can be the Nu itself or a protected form of this nucleophile group).

Visible-light-induced Ci-S bond activation: Facile access to 1,4-diketones from β-ketosulfones

A novel method for the synthesis of 1,4-diketones from β-ketosulfones was developed by means of a visible light-induced Ci￡S bond activation process. Symmetrical and unsymmetrical 1,4-diketones can be easily prepared in moderate to good yields. A new and efficient method for the synthesis of 1,4-diketones from β-ketosulfones was developed by means of a visible-light-induced Ci￡S bond activation process (see scheme). Symmetrical and unsymmetrical 1,4-diketones can be easily prepared in moderate to good yields.