Iron-catalysed 1,2-acyl migration of tertiary α-azido ketones and 2-azido-1,3-dicarbonyl compounds

被引：17
|
作者：
Yang, Tonghao [1 ]
Lin, Yajun [1 ]
Yang, Chaoqun [1 ]
Yu, Wei [1 ]
机构：
[1] Lanzhou Univ, Coll Chem & Chem Engn, State Key Lab Appl Organ Chem, Lanzhou 730000, Gansu, Peoples R China
来源：
GREEN CHEMISTRY | 2019年 / 21卷 / 22期
基金：
中国国家自然科学基金;
关键词：
H BOND AMINATION; TRIBUTYLTIN HYDRIDE; RING-EXPANSION; IMIDO; COMPLEXES; ESTERS; REARRANGEMENT; CONSTRUCTION; ENAMIDES; ACCESS;
D O I：
10.1039/c9gc02085c
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Iron-catalysed 1,2-acyl migration of tertiary alpha-azido ketones and 2-azido-1,3-dicarbonyl compounds provides a simple and atom-economical approach toward enamides and isoquinolones. This paper reports two catalyst systems for these transformations which employ iron(ii) complexes [Fe(dpbz)]Br-2 (dpbz = 1,2-bis(diphenylphosphino)benzene) and FeBr2/Et3N, respectively. [Fe(dpbz)]Br-2 was found to be highly effective at converting 2-azido-2,3-dihydro-1H-inden-1-ones to isoquinolones. The reagent combination of FeBr2/Et3N, on the other hand, exhibited a broader catalytic scope, owing to the beneficial effect of Et3N. This latter catalyst system enables 2-azido-2-methyl-1,3-dicarbonyl compounds to be converted to the corresponding enamides under mild conditions in good yields.
引用
收藏
页码：6097 / 6102
页数：6
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