Palladium-Catalyzed N-Acylation of Monosubstituted Ureas Using Near-Stoichiometric Carbon Monoxide

被引：54
|
作者：
Bjerglund, Klaus
Lindhardt, Anders T.
Skrydstrup, Troels [1 ]
机构：
[1] Aarhus Univ, Ctr Insoluble Prot Struct inSPIN, Dept Chem, Langelandsgade 140, DK-8000 Aarhus, Denmark
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 77卷 / 08期
基金：
新加坡国家研究基金会;
关键词：
HETEROARYL BROMIDES; SITU GENERATION; ARYL BROMIDES; EX-SITU; CARBONYLATION; CO; AMINOCARBONYLATION; MO(CO)(6); CONVENIENT; COMPLEXES;
D O I：
10.1021/jo3000767
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The palladium-catalyzed carbonylation of urea derivatives with aryl iodides and bromides afforded N-benzoyl ureas (20 examples) in yields attaining quantitative via the application of near-stoichiometric amounts of carbon monoxide generated from the decarbonylation of the CO precursor, 9-methylfluorene-9-carbonyl chloride. The synthetic protocol displayed good functional group tolerance. The methodology is also highly suitable for C-13 isotope labeling, which was demonstrated through the synthesis of three benzoyl ureas, including the insecticide triflumuron, whereby (CO)-C-13 was incorporated into the core structure.
引用
收藏
页码：3793 / 3799
页数：7
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