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反应速率和范围的增加:空气中微波加热氨基羰基化反应中反应迟缓的胺类

Increasing rates and scope of reactions: sluggish amines in microwave-heated aminocarbonylation reactions under air.

作者信息

Wannberg Johan, Larhed Mats

机构信息

Department of Organic Pharmaceutical Chemistry, Uppsala University, Biomedical Centre, Box-574, SE-751 23 Uppsala, Sweden.

出版信息

J Org Chem. 2003 Jul 11;68(14):5750-3. doi: 10.1021/jo034382d.

Abstract

Commercially available molybdenum hexacarbonyl serves as a convenient and solid carbon monoxide source in palladium-catalyzed aminocarbonylations of aryl bromides and iodides. This improved microwave protocol, relying on DBU as base and THF as solvent, enables rapid couplings using otherwise sluggish anilines, tert-butylamine, and free amino acids. In addition, Cr(CO)(6) and W(CO)(6) were found to be useful alternative CO-releasing reagents. Altogether, 16 different aromatic amides were synthesized under air in 35-95% yield after only 15 min of controlled microwave irradiation.

摘要

市售的六羰基钼在钯催化的芳基溴化物和碘化物的氨羰基化反应中是一种方便且稳定的一氧化碳源。这种改进的微波方法,以DBU为碱、THF为溶剂,能够使用原本反应缓慢的苯胺、叔丁胺和游离氨基酸实现快速偶联。此外,发现Cr(CO)₆和W(CO)₆是有用的替代一氧化碳释放试剂。总共,在空气氛围下,经过仅15分钟的受控微波辐射后,以35% - 95%的产率合成了16种不同的芳香酰胺。

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