Metal-free iodic acid-triggered cascade cyclization of alkenes with N-hydroxyphthalimide: A simple and mild access to aminooxylated 3,3-disubstituted 2-oxindoles

被引：3

作者：

Zhang, Ming-Zhong ^{[1
]}

Li, Yan ^{[1
]}

Zhang, Jiao ^{[1
]}

Bao, Xin ^{[1
]}

Yuan, Ya-Wen ^{[1
]}

Chen, Jie ^{[1
]}

Chen, Feng-Gui ^{[1
]}

机构：

[1] Yangtze Normal Univ, Coll Chem & Chem Engn, Chongqing 408100, Peoples R China

来源：

TETRAHEDRON LETTERS | 2021年 / 67卷

关键词：

Radical cyclization; Alkenes; Metal-free; Catalyst-free; Initiator; TANDEM RADICAL CYCLIZATION; C-H BONDS; ACTIVATED ALKENES; CATALYZED ARYLSULFONYLATION; OXIDATIVE CARBOAZIDATION; SULFONATED OXINDOLES; ARYLACRYLAMIDES; ACRYLAMIDES; TRIFLUOROMETHYLATION; DIFUNCTIONALIZATION;

D O I：

10.1016/j.tetlet.2021.152874

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient iodic acid-triggered radical cyclization of alkenes with N-hydroxyphthalimide (NHPI) is described. This operationally simple method was conducted under metal- and catalyst-free conditions, producing the precious aminooxylated 3,3-disubstituted 2-oxindoles in good to high yields. Green and readily available HIO3 was used as a sole and safe initiator, making this protocol highly advantageous. (C) 2021 Elsevier Ltd. All rights reserved.

引用

页数：5

共 7 条

[1] Metal-free trifluoroethylation of activated alkenes: rapid access to construct fluorinated 3,3-disubstituted 2-oxindoles
Mai, Wen-Peng
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Yang, Liang-Ru
Xiao, Yong-Mei
TETRAHEDRON, 2015, 71 (44) : 8416 - 8423
[2] Metal-free synthesis of 3,3-disubstituted oxindoles via 1,2-alkylarylation of activated alkenes with alcohols
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[3] A general route to fluorinated 3,3-disubstituted 2-oxindoles via a photoinduced radical cyclization of N-arylacrylamides under catalyst-free conditions
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[4] Metal-Free Synthesis of Oxazolidine-2,4-diones and 3,3-Disubstituted Oxindoles via ICl-Induced Cyclization
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[5] TfOH-Catalyzed Cascade Reaction: Metal-Free Access to 3,3-Disubstituted Phthalides from o-Alkynylbenzoic Acids
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JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (18): : 12924 - 12934
[6] Photoredox-Catalyzed Tandem Radical Cyclization of N-Arylacrylamides: General Methods To Construct Fluorinated 3,3-Disubstituted 2-Oxindoles Using Fluoroalkylsulfonyl Chlorides
Tang, Xiao-Jun
Thomoson, Charles S.
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ORGANIC LETTERS, 2014, 16 (17) : 4594 - 4597
[7] Metal-Free Tandem Rearrangement/Lactonization: Access to 3,3-Disubstituted Benzofuran-2-(3H)-ones
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