Application of 1,4-pentanediol as a renewable solvent for copper-catalyzed Ullmann-type coupling reactions

被引：0

作者：

Arvai, Csaba ^{[1
]}

Mika, Laszlo T. ^{[1
]}

机构：

[1] Budapest Univ Technol & Econ, Fac Chem Technol & Biotechnol, Dept Chem & Environm Proc Engn, Muegyet Rkp 3, H-1111 Budapest, Hungary

来源：

JOURNAL OF ORGANOMETALLIC CHEMISTRY | 2024年 / 1005卷

关键词：

Alternative solvent; 1,4-Pentanediol; Cross-coupling; Ullmann-coupling; Copper-catalysis; N-ARYLATION; C-N; ARYL BROMIDES; AMINES; LIGAND; TEMPERATURE; ALKYLAMINES; CONVERSION; CHEMISTRY; IODIDES;

D O I：

10.1016/j.jorganchem.2023.122976

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

It was demonstrated that 1,4-pentanediol as a biomass-originated polar protic solvent could be utilized as an alternative reaction medium for copper-catalyzed Ullmann-type coupling reactions of aryl iodides and various amines under mild conditions. The effect of the copper source, the base, the water, and the gamma-valerolactone content of the reaction mixture on the reaction performance was investigated. Eighteen cross-coupling products were isolated with yields of 11-69 %, and high purity (>98 %). Two O-arylated products, 4-phenoxypentan-1-ol and 5-phenoxypentan-2-ol were characterized. The recycling of the solvents after product isolation was also demonstrated. These results represent an example that proves that biomass-derived safer solvents can be utilized in common, industrially important transformations.

引用

页数：6

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