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Iron‐Catalyzed Decarboxylative (4+1) Cycloadditions: Exploiting the Reactivity of Ambident Iron‐Stabilized Intermediates
Author(s) -
Wang Qiang,
Qi Xiaotian,
Lu LiangQiu,
Li TianRen,
Yuan ZhiGuang,
Zhang Kai,
Li BinJie,
Lan Yu,
Xiao WenJing
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201510413
Subject(s) - cycloaddition , chemistry , indoline , reactivity (psychology) , allylic rearrangement , catalysis , decarboxylation , density functional theory , sulfur , ethylene , organic chemistry , computational chemistry , combinatorial chemistry , medicine , alternative medicine , pathology
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.