5724-06-1

Upstream product

• 123-11-5 4-methoxy-benzaldehyde 
• 61691-82-5 1'-acetoxyestragole 
• 104-88-1 4-chlorobenzaldehyde 
• 637-69-4 4-Methoxystyrene 
• 591-80-0 pent-4-enoic acid 
• 124-38-9 carbon dioxide 
• 16510-27-3 1-(cyclopropylmethyl)-4-methoxybenzene 
• 60633-18-3 (3-carboxy-propyl)triphenylphosphonium chloride 
• 212777-65-6 dimethyl [(2E)-3-(4-methoxyphenyl)prop-2-en-1-yl]malonate 
• 90841-43-3 (E)-4-methoxycinnamyl bromide 
• 53484-50-7 (E)-p-methoxy-cinnamyl alcohol 
• 24393-56-4 ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate 
• 696-62-8 para-iodoanisole 
• 55088-84-1 4-methoxybenzylidenecyclopropane 

Downstream Products

• 24962-83-2 (±)-5-(4-methoxybenzyl)dihydrofuran-2(3H)-one 
• 24962-85-4 (+/-)-5-(4-methoxyphenylcarbonyl)dihydrofuran-2(3H)-one 
• 1415637-35-2 (5R,6S)-5-iodo-6-(4-methoxyphenyl)tetrahydro-2H-pyran-2-one 
• 1374877-78-7 (2S,3R)-3-bromo-2-(4-methoxyphenyl)-1-(4-nitrophenylsulfonyl)pyrrolidine 

Relevant academic research and scientific papers

Synthesis of Antitricyclic Morpholine Derivatives through Iodine(III)-Mediated Intramolecular Umpolung Cycloaddition of Olefins

A (diacetoxyiodo)benzene-mediated intramolecular cycloaddition of olefins to construct tricyclic morpholines is presented. A series of substituted tricyclic morpholines were obtained in one-step simple operation under mild conditions, and the NMR studies

HFIP Solvent Enables Alcohols to Act as Alkylating Agents in Stereoselective Heterocyclization

A new method for the stereoselective synthesis of highly functionalized oxygen heterocycles using allyl or benzyl alcohols as alkylating agents is presented. The process is efficient and atom economic, generating water as the only stoichiometric byproduct. Substoichiometric amounts of Ti(OiPr)4 in HFIP solvent are key to this reactivity, and the method tolerates a broad substitution pattern on both the alcohol initiator and homoallylic alcohol substrate. Preliminary mechanistic studies reveal in situ formation of a titanium complex with HFIP which may initiate the cyclization reaction. Further stereoselective functionalization of the products allows access to a diverse range of interesting heterocyclic structures.

Carboxylation of benzylic and aliphatic C-H bonds with CO2 induced by light/ketone/nickel

A photoinduced carboxylation reaction of benzylic and aliphatic C-H bonds with CO2 is developed. Toluene derivatives capture gaseous CO2 at the benzylic position to produce phenylacetic acid derivatives when irradiated with UV light in the presence of an aromatic ketone, a nickel complex, and potassium tert-butoxide. Cyclohexane reacts with CO2 to furnish cyclohexanecar-boxylic acid under analogous reaction conditions. The present photoinduced carboxylation reaction provides a direct access from readily available hydrocarbons to the corresponding carboxylic acids with one carbon extension.

trans-Cyclooctenes as Halolactonization Catalysts

The strained olefins in trans-cyclooctenes serve as efficient catalysts for halolactonizations, including bromolactonizations and iodolactonizations. The trans-cyclooctene framework is essential for excellent catalytic performance, and the substituents also play important roles in determining efficiency. These results are the first demonstration of catalysis by a trans-cyclooctene.

Reversing the Regioselectivity of Halofunctionalization Reactions through Cooperative Photoredox and Copper Catalysis

Halofunctionalization of alkenes is a classical method for olefin difunctionalization. It gives rise to adducts which are found in many natural products and biologically active molecules, and offers a synthetic handle for further manipulation. Classically, this reaction is performed with an electrophilic halogen source and leads to regioselective formation of the halofunctionalized adducts. Herein, we demonstrate a reversal of the native regioselectivity for alkene halofunctionalization through the use of an acridinium photooxidant in conjunction with a copper cocatalyst.

Orthogonally protected 1,2-diols from electron-rich alkenes using metal-free olefin syn-dihydroxylation

A new method for the stereoselective metal-free syn-dihydroxylation of electron-rich olefins is reported, involving reaction with TEMPO/IBX in trifluoroethanol (TFE) or hexafluoroisopropanol (HFIP) and the addition of a suitable nucleophile. Orthogonally

Preparation of α-Acyloxy Ketones via Visible-Light-Driven Aerobic Oxo-Acyloxylation of Olefins with Carboxylic Acids

We developed a visible-light driven oxo-acyloxylation of aryl alkenes with carboxylic acids and molecular oxygen. A metal-free photoredox system, consisting of an acridinium photocatalyst, an organic base, and molecular sieve (MS) 4 ?, promotes chemoselective aerobic photooxidation of aryl alkenes. This approach may provide a green, practical, and metal-free protocol for a wide range of α-acyloxy ketones.

Anodic coupling of carboxylic acids to electron-rich double bonds: A surprising non-Kolbe pathway to lactones

Carboxylic acids have been electro-oxidatively coupled to electron-rich olefins to form lactones. Kolbe decarboxylation does not appear to be a significant competing pathway. Experimental results indicate that oxidation occurs at the olefin and that the reaction proceeds through a radical cation intermediate.

Direct catalytic anti-markovnikov hydroetherification of alkenols

A direct intramolecular anti-Markovnikov hydroetherification reaction of alkenols is described. By employing catalytic quantities of commercially available 9-mesityl-10-methylacridinium perchlorate and 2-phenylmalononitrile as a redox-cycling source of a

Aminothiocarbamate-catalyzed asymmetric bromolactonization of 1,2-disubstituted olefinic acids

An efficient and enantioselective bromolactonization of 1,2-disubstituted olefinic acids using an amino-thiocarbamate catalyst has been developed, resulting in the formation of δ-lactones containing two chiral centers with up to 99% yield, 95% ee.