Halogen Bonding Promoted Photoinduced Synthesis of 3,3-Disubstituted Oxindoles

被引：0

作者：

Chen, Kun-Quan ^{[1
]}

Zhang, Jia ^{[2
]}

Chen, Xiao-Bo ^{[2
]}

Sun, De-Qun ^{[2
]}

机构：

[1] Putian Univ, Sch Pharm & Med Technol, Key Lab Med Microecol, Putian 351100, Peoples R China

[2] Southwest Univ Sci & Technol, Sch Life Sci & Engn, Mianyang 621010, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2025年 / 90卷 / 18期

关键词：

FRIEDEL-CRAFTS ALKYLATION; CONSTRUCTION; FUNCTIONALIZATION; ACTIVATION; ARENES;

D O I：

10.1021/acs.joc.4c02963

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A photoinduced and catalyst-free radical cyclization process for the synthesis of 3,3-disubstituted oxindoles is reported. This method utilizes readily available alpha-bromoanilides as substrates, showcasing a broad substrate scope. The reaction mechanism is facilitated by a photoactivated charge transfer complex based on the halogen bonding of alpha-bromoanilide with TMG and alcohol.

引用

页码：6318 / 6322

页数：5

共 60 条

[1] Comparison of indolidan analog binding sites of drug antibody and sarcoplasmic reticulum with inhibition of cyclic AMP phosphodiesterase [J].

Ashikaga, T ;

Robertson, DW ;

Sportsman, RJ ;

Strada, SJ ;

Thompson, WJ .

JOURNAL OF RECEPTOR AND SIGNAL TRANSDUCTION RESEARCH, 1996, 16 (5-6) :315-337

[2] An Organocatalytic Asymmetric Friedel-Crafts Addition/Fluorination Sequence: Construction of Oxindole-Pyrazolone Conjugates Bearing Vicinal Tetrasubstituted Stereocenters [J].

Bao, Xiaoze ;

Wang, Baomin ;

Cui, Longchen ;

Zhu, Guodong ;

He, Yuli ;

Qu, Jingping ;

Song, Yuming .

ORGANIC LETTERS, 2015, 17 (21) :5168-5171

[3] Aerobic Radical-Cascade Alkylation/Cyclization of α,β-Unsaturated Amides: an Efficient Approach to Quaternary Oxindoles [J].

Biswas, Promita ;

Paul, Subhasis ;

Guin, Joyram .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (27) :7756-7760

[4] Stereoselective synthesis and applications of spirocyclic oxindoles [J].

Boddy, Alexander J. ;

Bull, James A. .

ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (05) :1026-1084

[5] Halogen Bonding in Organic Synthesis and Organocatalysis [J].

Bulfield, David ;

Huber, Stefan M. .

CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (41) :14434-14450

[6] Development of Synthetic Methodologies via Catalytic Enantioselective Synthesis of 3,3-Disubstituted Oxindoles [J].

Cao, Zhong-Yan ;

Zhou, Feng ;

Zhou, Jian .

ACCOUNTS OF CHEMICAL RESEARCH, 2018, 51 (06) :1443-1454

[7] The Halogen Bond [J].

Cavallo, Gabriella ;

Metrangolo, Pierangelo ;

Milani, Roberto ;

Pilati, Tullio ;

Priimagi, Arri ;

Resnati, Giuseppe ;

Terraneo, Giancarlo .

CHEMICAL REVIEWS, 2016, 116 (04) :2478-2601

[8] Intramolecular 1,5-H transfer reaction of aryl iodides through visible-light photoredox catalysis: a concise method for the synthesis of natural product scaffolds [J].

Chen, Jian-Qiang ;

Wei, Yun-Long ;

Xu, Guo-Qiang ;

Liang, Yong-Min ;

Xu, Peng-Fei .

CHEMICAL COMMUNICATIONS, 2016, 52 (38) :6455-6458

[9] N-Heterocyclic Nitreniums Can Be Employed as Photoredox Catalysts for the Single-Electron Reduction of Aryl Halides [J].

Chen, Kun-Quan ;

Zhang, Bei-Bei ;

Wang, Zhi-Xiang ;

Chen, Xiang-Yu .

ORGANIC LETTERS, 2022, 24 (25) :4598-4602

[10] Recent advances in organocatalytic methods for the synthesis of disubstituted 2-and 3-indolinones [J].

Dalpozzo, Renato ;

Bartoli, Giuseppe ;

Bencivenni, Giorgio .

CHEMICAL SOCIETY REVIEWS, 2012, 41 (21) :7247-7290

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