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

被引：55

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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