Synergistic-Catalysis-Enabled Reaction of 2-Indolymethanols with Oxonium Ylides for the Construction of 3-Indolyl-3-Alkoxy Oxindole Frameworks

被引：68
作者：
Ma, Chun [1 ]
Zhou, Jia-Yu [1 ]
Zhang, Yi-Zhu [1 ]
Jiao, Yinchun [2 ]
Mei, Guang-Jian [1 ]
Shi, Feng [1 ]
机构：
[1] Jiangsu Normal Univ, Sch Chem & Mat Sci, Xuzhou 221116, Jiangsu, Peoples R China
[2] Hunan Univ Sci & Technol, Sch Chem & Chem Engn, Xiangtan 411201, Peoples R China
来源：
CHEMISTRY-AN ASIAN JOURNAL | 2018年 / 13卷 / 17期
基金：
中国国家自然科学基金;
关键词：
cooperative effects; multicomponent reactions; oxindoles; synergistic catalysis; synthetic methods; ENANTIOSELECTIVE 3-COMPONENT REACTIONS; BRONSTED-ACID CATALYSIS; FRIEDEL-CRAFTS REACTION; INDOLE-DERIVATIVES; PHOSPHORIC-ACID; ASYMMETRIC REACTIONS; ALPHA-ALKYLATION; MULTICOMPONENT REACTIONS; COOPERATIVE CATALYSIS; S(N)1-TYPE REACTION;
D O I：
10.1002/asia.201800620
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A synergistic-catalysis-enabled reaction of 2-indolymethanols with oxonium ylides has been established that makes use of a three-component reaction between 3-diazooxindoles, alcohols, and 2-indolymethanols under the cooperative catalysis of a metal complex and a BrOnsted acid. This reaction has not only provided a new approach for the construction of 3-indolyl-3-alkoxy oxindole scaffolds by utilizing the C3-electrophilicity of an indole, but it is also the first example of a nucleophilic addition of a metal-associated ylide to 2-indolylmethanols. In addition, this reaction also includes a rarely reported trapping of onium ylides with aryl electrophiles.
引用
收藏
页码：2549 / 2558
页数：10
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