81701-30-6

Upstream product

• 140-67-0 Estragole 
• 64-19-7 acetic acid 
• 4180-23-8 E-1-(4'-methoxyphenyl)prop-1-ene 
• 930-68-7 cyclohexenone 
• 61691-82-5 1'-acetoxyestragole 
• 943-89-5 (E)-3-(4-methoxyphenyl)acrylic acid 
• 24393-56-4 ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate 
• 591-87-7 Allyl acetate 
• 100-66-3 methoxybenzene 
• 637-69-4 4-Methoxystyrene 
• 123-11-5 4-methoxy-benzaldehyde 
• 108-24-7 acetic anhydride 
• 53484-50-7 p-methoxycinnamyl alcohol 
• 75-36-5 acetyl chloride 

Downstream Products

• 189884-50-2 (+)-2-[1-(4-methoxy-phenyl)-allyl]-malonic acid dimethyl ester 
• 212777-65-6 dimethyl [(2E)-3-(4-methoxyphenyl)prop-2-en-1-yl]malonate 
• 30277-63-5 3-methoxy-3-(4-methoxyphenyl)propene 
• 53484-53-0 (E)-1-methoxy-4-(3-methoxyprop-1-en-1-yl)benzene 
• 1223575-23-2 1-(3-butylsulfanyl-propenyl)-4-methoxy-benzene 
• 1223575-22-1 1-(3-benzylsulfanyl-propenyl)-4-methoxy-benzene 
• 1223575-30-1 C₁₆H₁₅ClOS 
• 123-11-5 4-methoxy-benzaldehyde 

Relevant academic research and scientific papers

Enantioselective synthesis of 3-substituted dihydrobenzofurans through iridium-catalyzed intramolecular hydroarylation

Intramolecular hydroarylationviaC-H activation is one of the most powerful methods to synthesize carbo- and heterocyclic compounds, whereas we still have room for developing a highly enantioselective variant of the reaction. Here we describe Ir-catalyzed enantioselective intramolecular hydroarylation ofm-allyloxyphenyl ketones. The enantioselective cyclization was efficiently catalyzed by a cationic iridium complex coordinated with a conventional chiral bisphosphine ligand to give benzofurans in high yields with high enantioselectivity. A carbonyl group of ketones functioned as an effective directing group for the C-H activation. In terms of synthetic utility, we also achieved one-pot synthesis of chiral 3-substituted dihydrobenzofurans from readily available allylic carbonates andm-hydroxyacetophenonesviasequential Pd-catalyzed allylic substitution and Ir-catalyzed intramolecular hydroarylation.

Palladium-Catalyzed Oxidative Allylic Alkylation of N -Hydroxy-imides

A palladium-catalyzed oxidative C-H allylic alkylation of N -hydroxyimides has been developed. This transformation provided valuable N -allyloxypyrrolidinediones in moderate to excellent yields using operationally simple, ligand free, and mild reaction co

Palladium-catalyzed allylic C-H oxidation under simple operation and mild conditions

We discovered an effective and simple system (Pd/BQ/air/r.t.) for making allylic alcohols through Pd-catalyzed allylic C-H bond functionalization. This approach exhibits advantages due to its simple operation, mild conditions, and environmentally benign features. By modifying reaction conditions, it can be suitable for preparing unsaturated aldehydes, allylic esters, ethers, and amines.

Sequential Palladium-Catalyzed Allylic Alkylation/retro-Dieckmann Fragmentation Strategy for the Synthesis of α-Substituted Acrylonitriles

A straightforward synthesis of α-substituted acrylonitriles is described using 4-cyano-3-oxotetrahydro-thiophene (c-THT) as an acrylonitrile surrogate. This unprecedented two-step sequence featuring a palladium-catalyzed allylic alkylation (Pd-AA) and a retro-Dieckmann fragmentation provides a general entry into diversely substituted 1,4-dienes.

Size-Exclusion Borane-Catalyzed Domino 1,3-Allylic/Reductive Ireland–Claisen Rearrangements: Impact of the Electronic and Structural Parameters on the 1,3-Allylic Shift Aptitude

The reductive Ireland–Claisen rearrangement through borane-mediated hydrosilylation is reported. The method employs a borane catalyst with a special structural design and affords access to synthetically relevant products with high diastereoselectivity. Depending on electronic and structural parameters, the reaction can be coupled with a 1,3-allylic shift, thus the valence isomer of the Ireland–Claisen product is formed.

S,O-ligand-promoted palladium-catalyzed C–H olefination of arenes with allylic substrates

An efficient catalytic system for the C–H olefination of arenes with different allylic substrates is reported. The catalytic system is based on Pd(OAc)2 and a readily accessible bidentate S,O-ligand. The methodology shows high activity with a wide range of arenes, including bulky and, electron-rich and -poor arenes. The applicability of this catalyst is demonstrated in the late-stage functionalization of the complex molecule O-methylestrone.

Highly Enantioselective, Base-Free Synthesis of α-Quaternary Succinimides through Catalytic Asymmetric Allylic Alkylation

The synthesis of diversely substituted five-membered ring succinimide derivatives is reported featuring a direct, base-free, palladium-catalyzed asymmetric allylic alkylation. The method allows a straightforward access to the desired heterocyclic scaffold bearing an all-carbon α-quaternary stereogenic center in high yields and good to excellent enantioselectivities. To further demonstrate the synthetic utility of the method, the allylated products were further converted to various versatile chiral building blocks, including a chiral pyrrolidine and a spirocyclic derivative, using selective transformations.

Hydroamination versus Allylic Amination in Iridium-Catalyzed Reactions of Allylic Acetates with Amines: 1,3-Aminoalcohols via Ester-Directed Regioselectivity

In the presence of a neutral dppf-modified iridium catalyst and Cs2CO3, linear allylic acetates react with primary amines to form products of hydroamination with complete 1,3-regioselectivity. The collective data, including deuterium labeling studies, corroborate a catalytic mechanism involving rapid, reversible acetate-directed aminoiridation with inner-sphere/outer-sphere crossover followed by turnover-limiting proto-demetalation mediated by amine.

Heterotelechelic Polymers by Ring-Opening Metathesis and Regioselective Chain Transfer

Heterotelechelic polymers were synthesized by a kinetic telechelic ring-opening metathesis polymerization method relying on the regioselective cross-metathesis of the propagating Grubbs’ first-generation catalyst with cinnamyl alcohol derivatives. This procedure allowed the synthesis of hetero-bis-end-functional polymers in a one-pot setup. The molecular weight of the polymers could be controlled by varying the ratio between cinnamyl alcohol derivatives and monomer. The end functional groups can be changed using different aromatically substituted cinnamyl alcohol derivatives. Different monomers were investigated and the presence of the functional groups was shown by NMR spectroscopy and MALDI-ToF mass spectrometry. Labeling experiments with dyes were conducted to demonstrate the orthogonal addressability of both chain ends of the heterotelechelic polymers obtained.

Hydrazone-Pd-catalyzed direct intermolecular reaction of: O -alkynylphenols with allylic acetates

We found that the hydrazone-Pd-catalyzed direct intermolecular reaction of o-alkynylphenols with allylic acetates afforded the corresponding 2-substituted-3-allylbenzofuran derivatives. This reaction proceeded smoothly at room temperature using a hydrazon