Photoinduced Metal-Free Decarboxylative Fluoroalkylation of Alkenes for the Synthesis of N-Arylbutanamides and Oxindoles

被引：2

作者：

Ji, Yi-Gang ^{[1
]}

Li, Zhuo-Hong ^{[1
]}

Yang, Yu-Qing ^{[1
]}

Yang, Xiaohu ^{[3
]}

Yang, Wen-Chao ^{[2
]}

机构：

[1] Jiangsu Second Normal Univ, Coll Life Sci & Chem, Jiangsu Key Lab Biofunct Mol, Nanjing 210013, Peoples R China

[2] Yangzhou Univ, Sch Plant Protect, Yangzhou 225009, Peoples R China

[3] Zhejiang Hosp, Dept Pharm, Hangzhou 310013, Zhejiang, Peoples R China

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2024年 / 30卷 / 68期

关键词：

decarboxylation; fluoroalkylation; photochemical; metal-free; C-H TRIFLUOROMETHYLATION; OXIDATIVE DECARBOXYLATION; ACID-DERIVATIVES; CARBOXYLIC-ACIDS; ACCESS; ARENES; DIFLUOROACETATES; CATALYST;

D O I：

10.1002/chem.202402891

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The visible light-induced decarboxylative cascade reaction of fluoroalkyl carboxylic acids has been achieved for the efficient synthesis of fluorinated compounds. However, most of the transformations rely on noble iridium metal complex. Herein, a visible light-induced metal-free decarboxylative cascade reaction of fluoroalkyl carboxylic acids has been realized. This protocol features simple operation, transition metal free, and good functional group tolerance.

引用

页数：4

共 66 条

[1] Synthesis and antibacterial activity of 1-(2-fluorovinyl)-7-substituted-4-quinolone-3-carboxylic acid derivatives, conformationally restricted analogues of fleroxacin [J].

Asahina, Y ;

Iwase, K ;

Iinuma, F ;

Hosaka, M ;

Ishizaki, T .

JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (09) :3194-3202

[2] Scalable decarboxylative trifluoromethylation by ion-shielding heterogeneous photoelectrocatalysis [J].

Chen, Yixin ;

He, Yuchen ;

Gao, Yong ;

Xue, Jiakun ;

Qu, Wei ;

Xuan, Jun ;

Mo, Yiming .

SCIENCE, 2024, 384 (6696) :670-676

[3] Silver-catalyzed stereoselective C-4 arylthiodifluoromethylation of coumarin-3-carboxylic acids via a double decarboxylative strategy [J].

Chen, Zhiwei ;

Sun, Jie ;

Ke, Zhiwei ;

Huang, Xiaoxiao ;

Li, Ziwei .

ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (03) :757-763

[4] Fe(III)-Catalyzed Decarboxylative C3-Difluoroarylmethylation of Coumarins with α,α-Difluoroarylacetic Acids [J].

Chen, Zhiwei ;

Bai, Xiang ;

Sun, Jie ;

Xu, Yicheng .

JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (12) :7674-7682

[5] Promising reagents for difluoroalkylation [J].

Dong, Dao-Qing ;

Yang, Huan ;

Shi, Jun-Lian ;

Si, Wen-Jia ;

Wang, Zu-Li ;

Xu, Xin-Ming .

ORGANIC CHEMISTRY FRONTIERS, 2020, 7 (17) :2538-2575

[6] Difluoroalkylation of Anilines via Photoinduced Methods [J].

Gallego-Gamo, Albert ;

Granados, Albert ;

Pleixats, Roser ;

Gimbert-Surinach, Carolina ;

Vallribera, Adelina .

JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (17) :12585-12596

[7] Visible-Light-Initiated Difunctionalization of Quinoxalin-2(1H)-ones with Acyloxy Nitroso Compounds [J].

Gao, Runye ;

Wang, Fang ;

Geng, Xiao ;

Li, Chuan-Ying ;

Wang, Lei .

ORGANIC LETTERS, 2022, 24 (39) :7118-7122

[8] Synthesis of non-anomeric C-glycosyl pyrazolidinone derivatives via visible-light photoredox catalysis [J].

Goncalves, Renan. O. ;

Oliveira, Pedro H. R. ;

de Jesus, Iva S. ;

Debia, Natali P. ;

Ludtke, Diogo S. ;

Paixao, Marcio W. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (27) :5516-5520

[9] Hydrodecarboxylation of Carboxylic and Malonic Acid Derivatives via Organic Photoredox Catalysis: Substrate Scope and Mechanistic Insight [J].

Griffin, Jeremy D. ;

Zeller, Mary A. ;

Nicewicz, David A. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (35) :11340-11348

[10] Visible-light-initiated tandem synthesis of difluoromethylated oxindoles in 2-MeTHF under additive-, metal catalyst-, external photosensitizer-free and mild conditions [J].

Gui, Qing-Wen ;

Teng, Fan ;

Li, Zhou-Chao ;

Xiong, Zhi-Yuan ;

Jin, Xue-Feng ;

Lin, Ying-Wu ;

Cao, Zhong ;

He, Wei-Min .

CHINESE CHEMICAL LETTERS, 2021, 32 (06) :1907-1910

← 1 2 3 4 5 6 7 →