824431-48-3Relevant academic research and scientific papers
Catalytic Hydroetherification of Unactivated Alkenes Enabled by Proton-Coupled Electron Transfer
Knowles, Robert R.,Metrano, Anthony J.,Tsuchiya, Yuto,Tsui, Elaine
supporting information, p. 11845 - 11849 (2020/05/22)
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.
Nickel-catalyzed ring-opening cross-coupling of cyclic alkenyl ethers with arylboronic esters via carbon-oxygen bond cleavage
Ohtsuki, Akimichi,Sakurai, Shun,Tobisu, Mamoru,Chatani, Naoto
supporting information, p. 1277 - 1279 (2016/11/09)
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 bromocycloetherification by Lewis base/chiral Bronsted acid cooperative catalysis
Denmark, Scott E.,Burk, Matthew T.
supporting information; experimental part, p. 256 - 259 (2012/03/10)
A binary catalyst system for the enantioselective bromocycloetherification of 5-arylpentenols is described. The combination of an achiral Lewis base and a chiral Bronsted acid affords good enantioselectivities for the cyclization of Z configured 5-arylpen
Competition between alkenes in intramolecular ketene-alkene [2 + 2] cycloaddition: What does it take to win?
Belanger, Guillaume,Levesque, Francois,Paquet, Julie,Barbe, Guillaume
, p. 291 - 296 (2007/10/03)
(Chemical Equation Presented). In the course of developing a new synthetic methodology using ketenes in sequential cycloaddition steps, we were faced with a competition problem with molecules containing a ketene tethered to more than one reacting partner.
