110374-99-7

Upstream product

• 104-53-0 3-phenyl-propionaldehyde 
• 1560-56-1 (methyl-d3)triphenylphosphonium iodide 
• 54439-94-0 1,1-d₂-oct-1-ene 
• 75456-62-1 (4-methoxybut-3-en-1-yl)benzene 

Downstream Products

• 101335-78-8 methyl 4-(4-phenylbutyl)benzoate 

Relevant academic research and scientific papers

Copper-Catalyzed Synthesis of Stereodefined Cyclopropyl Bis(boronates) from Alkenes with CO as the C1 Source

A novel copper-catalyzed stereodefined procedure for the selective synthesis of cyclopropyl bis(boronates) from terminal alkenes has been developed. Various aliphatic alkenes were transformed into the desired bis(boronate ester)-substituted cyclopropanes

Electrochemical enol ether/olefin cross-metathesis in a lithium perchlorate/nitromethane electrolyte solution

(Chemical Equation Presented) Electrolytically generated four-membered-ring radical-cation intermediates are involved in the anodic olefin cross-metathesis of enol ethers and olefins in a lithium perchlorate/nitromethane electrolyte solution (see scheme). The reaction mechanism was investigated through deuterium-labeling studies.

sp3 Bis-Organometallic Reagents via Catalytic 1,1-Difunctionalization of Unactivated Olefins

A catalytic 1,1-difunctionalization of unactivated olefins en route to sp3 bis-organometallic B,B(Si)-reagents is described. The protocol is characterized by exceptional reaction rates, mild conditions, wide scope, and exquisite selectivity pattern, constituting a new platform to access sp3 bis-organometallics.

Mechanistic Interrogation of Co/Ni-Dual Catalyzed Hydroarylation

Cobalt/nickel-dual catalyzed hydroarylation of terminal olefins with iodoarenes builds complexity from readily available starting materials, with a high preference for the Markovnikov (branched) product. Here, we advance a mechanistic model of this reaction through the use of reaction progress kinetic analysis (RPKA), radical clock experiments, and stoichiometric studies. Through exclusion of competing hypotheses, we conclude that the reaction proceeds through an unprecedented alkylcobalt to nickel direct transmetalation. Demonstration of catalytic alkene prefunctionalization, via spectroscopic observation of an organocobalt species, distinguishes this Csp2-Csp3 cross-coupling method from a conventional transmetalation process, which employs a stoichiometric organometallic nucleophile, and from a bimetallic oxidative addition of an organohalide across nickel, described by radical scission and subsequent alkyl radical capture at a second nickel center. A refined understanding of the reaction leads to an optimized hydroarylation procedure that excludes exogenous oxidant, demonstrating that the transmetalation is net redox neutral. Catalytic alkene prefunctionalization by cobalt and engagement with nickel catalytic cycles through direct transmetalation provides a new platform to merge these two rich areas of chemistry in preparatively useful ways.

Modular Access to Substituted Azocanes via a Rhodium-Catalyzed Cycloaddition-Fragmentation Strategy

A short entry to substituted azocanes by a Rh-catalyzed cycloaddition-fragmentation process is described. Specifically, exposure of diverse N-cyclopropylacrylamides to phosphine-ligated cationic Rh(I) catalyst systems under a CO atmosphere enables the directed generation of rhodacyclopentanone intermediates. Subsequent insertion of the alkene component is followed by fragmentation to give the heterocyclic target. Stereochemical studies show, for the first time, that alkene insertion into rhodacyclopentanones can be reversible.

Sigmatropic Rearrangements of Deprotonated Allyl Phenylacetates in the Gas Phase

The ion C6H5C-HCO2CH2CH=CH2 undergoes competitive losses of C3H5OH and CO2 on collisional activation.The loss of C3H5OH proceeds through ion complex -(C6H5CH=C=O)> yielding C6H5CCO- and C3H5OH.This reaction occurs without prior ester equilibration C6H5C-HC(O)O*C3H5C6H5C-HC(O*)OC3H5.The elimination of CO2 follows rearrangement C6H5C-HCO2C3H5->C6H5(C3H5)CHCO2-.The rearrangement occurs through both six- and four-center transition states with the six-center (Claisen) rearrangement predominating.