78043-55-7Relevant articles and documents
Selective Approaches to α- and β-Arylated Vinyl Ethers
Bolm, Carsten,Domzalska-Pieczykolan, Anna,Funes-Ardoiz, Ignacio,Furman, Bart?omiej
supporting information, (2021/11/30)
We developed simple and efficient protocols for palladium-catalyzed regioselective α- and β-arylations of structurally diverse vinyl ethers. Both catalytic methods proceed under relatively mild reactions conditions applying to a broad substrate range including more complex compounds providing arylated glucal or isochromene. Lacking the common requirement of a large reagent excess, the transformations are highly economic and limiting the waste production. Results from computational studies (DFT) provided insight into the key factors determining the pronounced regioselectivities of the investigated reactions.
Styryl ether formation from benzyl alcohols under transition-metal-free basic DMSO conditions
Yang, Kai,Song, Qiuling
, p. 2267 - 2272 (2015/03/04)
A phenol-catalyzed aerobic oxidative styryl ether formation method was developed with benzyl alcohol under basic DMSO. Styryl ether was obtained after 12 hours of heating at 60-80 °C where DMSO was involved in the reaction as the extra carbon source. Control experiments indicated that both phenol and DMSO are crucial for the success of the reaction. A variety of styryl ethers were prepared smoothly from benzyl alcohols in good to excellent yields in an environmentally friendly way. This journal is
Non-carbonyl-stabilized metallocarbenoids in synthesis: The development of a tandem rhodium-catalyzed bamford-stevens/thermal aliphatic claisen rearrangement sequence
May, Jeremy A.,Stoltz, Brian M.
, p. 12426 - 12427 (2007/10/03)
A tandem rhodium-catalyzed Bamford-Stevens/Claisen rearrangement is presented. The tandem reaction uses Eschenmoser hydrazones for the in situ generation of non-carbonyl-stabilized diazo alkanes, which are presumably intercepted by Rh(II) catalysts to induce a 1,2-hydride migration. This sequence provides high levels of stereocontrol for the generation of simple acyclic (Z)-enol ethers. These enol ethers undergo either thermal or Lewis acid accelerated Claisen rearrangements to provide products of high diastereopurity. Also presented are cascade reactions, wherein a third chemical step occurs after the initial tandem sequence (i.e., Bamford-Stevens/Claisen/ene and Bamford-Stevens/Claisen/Cope). Copyright