Phosphonium Ionic Liquids-Accelerated Morita-Baylis-Hillman Reaction

Abstract

Phosphonium ionic liquids, due to their superior thermal stability and an inertness in weak basic reaction media, are receiving more and more attention. A series of phosphonium ionic liquids have been prepared starting from cheap tributylphosphine with various halogenated hydrocarbon. Then using 1,4-diazabicyclo[2.2.2]octane (DABCO) as catalyst and water-phosphonium ionic liquid composite system as reaction media, Morita-Baylis-Hillman reactions of a variety of aldehydes with acrylonitrile, methyl acrylate or acrylamide were studied. Experimental results showed that the composite system of phosphonium ionic liquid with water can effectivily accelerate the Morita-Baylis-Hillman reactions of aromatic aldehydes and aliphatic aldehydes, and fast reaction rate and high yield were obtained.

Application of Task-Specific Ionic liquids to Organic Synthesis

“…Zhao 等 [28] 还报道了以廉价的三丁基膦和各种卤代 烃为原料, 制备一系列季鏻离子液体 2, 然后与水组成 复合体系, 用于催化 Morita-Baylis-Hillman 反应. 考察 发现, 在该复合溶剂体系中, 各种醛与丙烯腈、丙烯酸 甲 酯 及 丙 烯 酰 胺 可 以 在 室 温 下 发 生 Morita-Baylis-Hillman 反应, 反应速率快、收率高.…”

Systematic study of the substitution effect on the tetrel bond between 1,4-diazabicyclo[2.2.2]octane and TH3X

“…48,49 Importantly, the MBH reaction of benzaldehyde with acrylamide under DABCO catalysis can be carried out in an aqueous system. 50 In addition, as a good linker, DABCO can also form structurally stable complexes with a variety of organic and organometallic compounds. 51 Similarly, there are some studies on the noncovalent interactions such as hydrogen and halogen bonds involved with DABCO.…”