Iron-Catalyzed Decarboxylative (4+1) Cycloadditions: Exploiting the Reactivity of Ambident Iron-Stabilized Intermediates

被引:105
|
作者
Wang, Qiang [1 ]
Qi, Xiaotian [2 ]
Lu, Liang-Qiu [1 ]
Li, Tian-Ren [1 ]
Yuan, Zhi-Guang [1 ]
Zhang, Kai [1 ]
Li, Bin-Fie [1 ]
Lan, Yu [2 ]
Xiao, Wen-Jing [1 ]
机构
[1] Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China
[2] Chongqing Univ, Sch Chem & Chem Engn, Chongqing 400030, Peoples R China
基金
中国国家自然科学基金;
关键词
cycloaddition; density-functional calculations; heterocycles; iron; ylides; SULFUR YLIDES; VINYLETHYLENE CARBONATES; ALLYLIC CARBONATES; CASCADE REACTIONS; CONSTRUCTION; CYCLOPROPANATION; INDOLES; FE; REGIOSELECTIVITY; ACTIVATION;
D O I
10.1002/anie.201510413
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The first example of iron-catalyzed decarboxylative (4+ 1) cycloaddition reactions is described in this publication. By using this method, a wide range of functionalized indoline products were prepared from easily available vinyl benzoxazinanones and sulfur ylides in high yields and selectivities. A possible reaction pathway involving an allylic iron intermediate is discussed based on a series of control experiments and density-functional theory calculations.
引用
收藏
页码:2840 / 2844
页数:5
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