Intermolecular α-Functionalization of Benzylamides with N-Nucleophiles via Oxidative Umpolung: Synthesis of Tetrasubstituted 3,3′-Oxindoles

被引：5
|
作者：
Wang, Yue [1 ]
Yu, Jiang-Ning [2 ]
Wang, Yang [1 ]
Shi, Feng [1 ,3 ]
机构：
[1] Changzhou Univ, Sch Petrochem Engn, Changzhou 213164, Peoples R China
[2] Henan Normal Univ, Sch Chem & Chem Engn, Xinxiang 453007, Peoples R China
[3] Jiangsu Normal Univ, Sch Chem & Mat Sci, Xuzhou 221116, Peoples R China
来源：
ORGANIC LETTERS | 2024年 / 26卷 / 28期
基金：
中国国家自然科学基金;
关键词：
FLUORINATION; KETONES; IODINE(III); DERIVATIVES; STRATEGIES; OXINDOLES; BOND; HF;
D O I：
10.1021/acs.orglett.4c02167
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A hypervalent iodine-mediated intermolecular alpha-umpolung reaction between alpha-aryl- or alkyl-substituted amides and benzotriazoles or purine derivatives as N-centered nucleophiles has been established. The reaction involves sequential intra/intermolecular oxidative C-N couplings in a controlled manner, affording tetrasubstituted 3,3 '-oxindoles in moderate to good yields. This approach efficiently addresses the challenges in constructing tetrasubstituted carbon centers via alpha-umpolung functionalizations of carbonyl compounds and serves as a new strategy for synthesizing biologically important 3,3 '-disubstituted oxindoles.
引用
收藏
页码：6041 / 6046
页数：6
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