Synthesis of 2-pyrrolidinone derivatives via N-heterocyclic carbene catalyzed radical tandem cyclization/coupling reactions

被引：15

作者：

Yin, Huiping ^{[1
]}

Huang, Tianjiao ^{[1
]}

Shi, Bai ^{[1
]}

Cao, Wei ^{[1
]}

Yu, Chenxia ^{[1
]}

Li, Tuanjie ^{[1
]}

Zhang, Kai ^{[1
]}

Yao, Changsheng ^{[1
]}

机构：

[1] Jiangsu Normal Univ, Sch Chem & Mat Sci, Jiangsu Key Lab Green Synthet Chem Funct Mat, Xuzhou 221116, Jiangsu, Peoples R China

来源：

ORGANIC CHEMISTRY FRONTIERS | 2023年 / 10卷 / 11期

基金：

中国国家自然科学基金;

关键词：

C-H ALKYLATION; ENANTIOSELECTIVE SYNTHESIS; GAMMA-LACTAMS; BIOLOGICAL IMPORTANCE; AMIDES; ALDEHYDES; PYRROLIDINONE; CONSTRUCTION; INHIBITORS; MECHANISM;

D O I：

10.1039/d3qo00544e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein, a practical, convenient and facile protocol for constructing highly functionalized 2-pyrrolidinone enabled by N-heterocyclic carbene (NHC)-catalyzed radical tandem cyclization has been developed (30 examples, up to 94% yield). This method is transition metal free, and shows broad substrate scope with excellent functional group compatibility and high efficiency.

引用

页码：2695 / 2700

页数：6

共 82 条

[1] A novel approach to chiral, nonracemic pyrrolidines by 5-exo-trig diastereoselective radical cyclization on acrylamides derived from(-)-8-aminomenthol [J].

Andrés, C ;

Duque-Soladana, JP ;

Pedrosa, R .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (12) :4282-4288

[2] An Overview on Biological Importance of Pyrrolone and Pyrrolidinone Derivatives as Promising Scaffolds [J].

Asif, M. ;

Alghamdi, S. .

RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 57 (10) :1700-1718

[3] Single-electron carbene catalysis in redox processes [J].

Bay, Anna, V ;

Scheidt, Karl A. .

TRENDS IN CHEMISTRY, 2022, 4 (04) :277-290

[4] Synthesis of Cyclohexanones by a Tandem Photocatalyzed Annulation [J].

Bay, Anna, V ;

Farnam, Emelia J. ;

Scheidt, Karl A. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2022, 144 (16) :7030-7037

[5] Light-Driven Carbene Catalysis for the Synthesis of Aliphatic and α-Amino Ketones [J].

Bay, Anna, V ;

Fitzpatrick, Keegan P. ;

Gonzalez-Montiel, Gisela A. ;

Farah, Abdikani Omar ;

Cheong, Paul Ha-Yeon ;

Scheidt, Karl A. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (33) :17925-17931

[6] Combined Photoredox and Carbene Catalysis for the Synthesis of Ketones from Carboxylic Acids [J].

Bay, Anna V. ;

Fitzpatrick, Keegan P. ;

Betori, Rick C. ;

Scheidt, Karl A. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (23) :9143-9148

[7] Recent advances in the chemistry and applications of N-heterocyclic carbenes [J].

Bellotti, Peter ;

Koy, Maximilian ;

Hopkinson, Matthew N. ;

Glorius, Frank .

NATURE REVIEWS CHEMISTRY, 2021, 5 (10) :711-725

[8] Organocatalytic umpolung: N-heterocyclic carbenes and beyond [J].

Bugaut, Xavier ;

Glorius, Frank .

CHEMICAL SOCIETY REVIEWS, 2012, 41 (09) :3511-3522

[9] N-Heterocyclic Carbene-Catalyzed 1,4-Alkylacylation of 1,3-Enynes [J].

Cai, Yuxing ;

Chen, Jiean ;

Huang, Yong .

ORGANIC LETTERS, 2021, 23 (23) :9251-9255

[10] Arylsulfonyl Radical Triggered 1,6-Enyne Cyclization: Synthesis of γ-Lactams Containing Alkenyl C-X Bonds [J].

Cao, Xia ;

Cheng, Xiao ;

Xuan, Jun .

ORGANIC LETTERS, 2018, 20 (02) :449-452

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