105401-84-1

Upstream product

• 5631-95-8 2,3-dichlorotetrahydro-2H-pyran 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 821-09-0 n-Pent-4-enyl alcohol 
• 696-62-8 para-iodoanisole 
• 5205-39-0 ethyl glutaroyl chloride 
• 1070-62-8 5-ethoxy-5-oxopentanoic acid 
• 1308888-10-9 5-(4-methoxycinnamyl)-2,2-dimethyl-1,3-dioxane-4,6-dione 
• 24680-50-0 4-methoxy-trans-cinnamaldehyde 
• 5390-04-5 pent-1-yn-5-ol 
• 154477-03-9 5-(4'-methoxyphenyl)-4-pentyn-1-ol 
• 637-69-4 4-Methoxystyrene 
• 61691-82-5 1'-acetoxyestragole 
• 123-11-5 4-methoxy-benzaldehyde 
• 100-66-3 methoxybenzene 

Downstream Products

• 102178-42-7 1t-(4-Methoxy-phenyl)-5-(4-nitro-2-methoxy-phenoxy)-penten-⁽¹⁾ 
• 14374-54-0 5-(4-methoxyphenyl)pentan-1-ol 
• 74357-24-7 (E)-5-(p-methoxyphenyl)-4-pentenyl 9-phenanthrenecarboxylate 
• 76978-41-1 (E)-5-(4-methoxyphenyl)pent-4-enal 
• 132723-33-2 2-(4-methoxyphenyl)-tetrahydro-2H-pyran 
• 66162-78-5 1-methyl-2-(4-methoxyphenyl)pyrrolidine 
• 148020-02-4 (E)-N-Methyl-5-(4-methoxyphenyl)pent-4-enylamine 
• 1334150-03-6 (2R,3S)-tetrahydro-2-(4-methoxyphenyl)-3-(phenylthio)-2H-pyran 

Relevant academic research and scientific papers

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.

Highly stereoselective hydrocarbation of terminal alkynes via Pt-Catalyzed Hydrosilylation/Pd-Catalyzed cross-coupling reactions

(matrix presented) The formal addition of an aryl-H or alkenyl-H bond across a terminal alkyne has been accomplished by the combination of platinum-catalyzed hydrosilylation followed by palladium-catalyzed cross-coupling. The use of the t-Bu3P-Pt(DVDS) catalyst in combination with tetramethyldisiloxane gave excellent regio- and stereoselectivity with a number of alkyne substrates. Subsequent, fluoride-promoted cross-coupling proceeded in high yield and stereospecificity for a variety of aryl halides.

Photooxidizing chromium catalysts for promoting radical cation cycloadditions

The photooxidizing capabilities of selected CrIII complexes for promoting radical cation cycloadditions are described. These complexes have sufficiently long-lived excited states to oxidize electron-rich alkenes, thereby initiating [4+2] processes. These metal species augment the spectrum of catalysts explored in photoredox systems, as they feature unique properties that can result in differential reactivity from the more commonly employed ruthenium or iridium catalysts. Spotlight on chromium: Selected CrIII complexes were investigated for promoting radical cation cycloadditions. These species have sufficiently long-lived excited states to oxidize electron-rich alkenes, thereby initiating [4+2] processes. These metal complexes augment the spectrum of catalysts explored in photoredox systems, featuring properties that can result in differential reactivity from the more common Ru or Ir catalysts.

Catalytic Hydroetherification of Unactivated Alkenes Enabled by Proton-Coupled Electron Transfer

We report a catalytic, light-driven method for the intramolecular hydroetherification of unactivated alkenols to furnish cyclic ether products. These reactions occur under visible-light irradiation in the presence of an IrIII-based photoredox catalyst, a Br?nsted base catalyst, and a hydrogen-atom transfer (HAT) co-catalyst. Reactive alkoxy radicals are proposed as key intermediates, generated by direct homolytic activation of alcohol O?H bonds through a proton-coupled electron-transfer mechanism. This method exhibits a broad substrate scope and high functional-group tolerance, and it accommodates a diverse range of alkene substitution patterns. Results demonstrating the extension of this catalytic system to carboetherification reactions are also presented.

Radical Cation Diels-Alder Reactions by TiO2 Photocatalysis

Radical cation Diels-Alder reactions by titanium dioxide (TiO2) photocatalysis in lithium perchlorate/nitromethane solution are described. TiO2 photocatalysis promotes reactions between electron-rich dienes and dienophiles, which would otherwise be difficult to accomplish due to electronic mismatching. The reactions are triggered by hole oxidation of the dienophile and are completed by the excited electron reduction of the radical cation intermediate at the dispersed surface in the absence of any sacrificial substrate.

Stereospecific Alkene Aziridination Using a Bifunctional Amino-Reagent: An Aza-Prilezhaev Reaction

In situ deprotection (TFA) of O-Ts activated N-Boc hydroxylamines triggers intramolecular aziridination of N-tethered alkenes to provide complex N-heterocyclic ring systems. Synthetic and computational studies corroborate a diastereospecific aza-Prilezhaev-type mechanism. The feasibility of related intermolecular alkene aziridinations is also demonstrated.

Radical Cation Cyclopropanations via Chromium Photooxidative Catalysis

The chromium photocatalyzed cyclopropanation of diazo reagents with electron-rich alkenes is described. The transformation occurs under mild conditions and features specific distinctions from traditional diazo-based cyclopropanations (e.g., avoiding β-hydride elimination, chemoselectivity considerations, etc.). The reaction appears to work most effectively using chromium catalysis, and a number of decorated cyclopropanes can be accessed in generally good yields.

Nickel-catalyzed ring-opening cross-coupling of cyclic alkenyl ethers with arylboronic esters via carbon-oxygen bond cleavage

We have developed a nickel-catalyzed cross-coupling reaction of cyclic alkenyl ethers with arylboronic esters that leads to the formation of unsaturated alcohols via ring-opening by the cleavage of a C(sp2)-O bond. The use of 1,3-dicyclohexylimidazol-2-ylidene as the ligand is essential to promote this cross-coupling process.

Enantioselective synthesis of 2-substituted and 3-substituted piperidines through a bromoaminocyclization process

A catalytic enantioselective bromocyclization of olefinic amides using amino-thiocarbamates as the catalysts has been developed. The resulting enantioenriched 2-substituted 3-bromopiperidines can readily be transformed to 3-substituted piperidines through

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