Organosoluble Copper Clusters as Precatalysts for Carbon−Heteroelement Bond-Forming Reactions:  Microwave and Conventional Heating

Abstract

The coupling of aryl iodides with alcohols under mild conditions has been explored using self-assembled octanuclear copper clusters as catalysts. Reactions involving tetrahydrofurfuryl alcohol were typically complete in 4-8 h at 110 degrees C using an oil bath or 1-3 h with microwave heating. High yields of alkyl aryl ethers were obtained with catalyst loadings as low as 0.4 mol % cluster.

Transition metals in organic synthesis: Highlights for the year 2005

“…(59)) [522]. Copper catalyzed intermolecular O-arylations of aryl iodides [523] and a copper-catalyzed intermolecular reaction was used in synthesis of aspercyclide C [524]. (59) A variety of amines and amides were coupled with aryl and alkenyl halides using palladium or copper catalysts [1,440,[525][526][527].…”

Ligand-Free Cu2O Nanowire Catalyzing C—N and C—O Coupling Reaction

“…Bolm 等 [6] 采用简单廉价无配体的铜催化体系催化 了亚砜胺和含氮杂环的芳基化, 使得 N-芳基化反应得 到了 64%～98%的产率. 2005 年 Stockland 等 [7] 研究了较 温和条件下铜盐催化无需配体的碘代芳烃与醇类的 C-O 缩合, 该反应在 110 ℃时反应 4～8 h 或微波加热 1～3 h 即可取得很高的产率. 魏俊发小组 [8] 研究了水相中无 配体条件下铜粉催化卤代芳烃的氨基化, 该体系只适用 于脂肪伯胺, 对仲胺、芳胺没有效果.…”

Microwave‐Heated Transition Metal‐Catalyzed Coupling Reactions

“…However, compared with the palladium-catalyzed counterparts, Ullmann reactions require larger amounts of catalyst and the reactions are generally slower. To deal with these problems, Stockland and co-workers developed a method using organosoluble copper clusters [187]. A series of alkyl aryl ethers were prepared using only 0.4 mol% of copper cluster to evaluate conventional and microwave heating (Scheme 15.93).…”