1174337-23-5Relevant articles and documents
A Phosphonium Ylide as a Ligand for [3 + 2] Coupling Reactions of Epoxides with Heterocumulenes under Mild Conditions
Hashimoto, Kousuke,Mori, Yoko,Suga, Hiroyuki,Toda, Yasunori
, p. 10980 - 10987 (2020)
The potential of carbonyl-stabilized phosphonium ylides as ligands for novel catalysis was explored. We found that the combination of phosphonium ylides and metal halide salts efficiently catalyzed the reaction of epoxides with carbon dioxide under mild c
Bifunctional organocatalysts for the conversion of CO2, epoxides and aryl amines to 3-aryl-2-oxazolidinones
Xie, Ya-Fei,Guo, Cheng,Shi, Lei,Peng, Bang-Hua,Liu, Ning
supporting information, p. 3497 - 3506 (2019/04/14)
A route to synthesize 3-aryl-2-oxazolidinones is developed, which is achieved through a three component reaction between CO2, aryl amines, and epoxides with a binary organocatalytic system composed of organocatalysts and DBU (1,8-diazabicyclo[5.4.0]undec-7-ene). The method allows wide scopes of epoxide and aryl amine substrates with various functional groups under mild reaction conditions. The control experiments indicate that a cyclic carbonate is formed via cycloaddition of epoxides with CO2, which further reacts with the β-amino alcohol originating from epoxides and aryl amines, resulting in the formation of 3-aryl-2-oxazolidinones finally.
Tetraarylphosphonium Salt-Catalyzed Synthesis of Oxazolidinones from Isocyanates and Epoxides
Toda, Yasunori,Gomyou, Shuto,Tanaka, Shoya,Komiyama, Yutaka,Kikuchi, Ayaka,Suga, Hiroyuki
supporting information, p. 5786 - 5789 (2017/11/10)
Preparation of a range of oxazolidinones, including enantioenriched N-aryl-substituted oxazolidinones, in which tetraarylphosphonium salts (TAPS) catalyze the [3 + 2] coupling reaction of isocyanates and epoxides effectively, is described. The key finding is a Br?nsted acid/halide ion bifunctional catalyst that can accelerate epoxide ring opening with high regioselectivity. Mechanistic studies disclosed that the ylide generated from TAPS, along with the formation of halohydrins, plays a crucial role in the reaction with isocyanates.