Visible-Light Photoredox-Catalyzed Dicarbofunctionalization of Styrenes with Oxime Esters and CO2: Multicomponent Reactions toward Cyanocarboxylic Acids and γ-Keto Acids

被引:27
作者
Bai, Junxue [1 ]
Li, Miao [1 ]
Zhou, Cong [1 ]
Sha, Yu [1 ]
Cheng, Jiang [1 ]
Sun, Jianwei [1 ,2 ]
Sun, Song [1 ]
机构
[1] Changzhou Univ, Sch Petrochem Engn, Jiangsu Key Lab Adv Catalyt Mat & Technol, Changzhou 213164, Peoples R China
[2] Hong Kong Univ Sci & Technol, Dept Chem, Kowloon, Hong Kong, Peoples R China
基金
中国国家自然科学基金;
关键词
CARBON-DIOXIDE; N-TOSYLHYDRAZONES; CARBOXYLATION; ALKYNES; HYDROCARBOXYLATION; TRANSFORMATION; ACCESS;
D O I
10.1021/acs.orglett.1c03938
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A photoredox-catalyzed dicarbofunctionalization of styrenes with oxime esters and CO2 has been achieved. Notably, a series of four-, five-, or six-membered cyclic ketone oximes worked well to furnish a wide range of epsilon-, zeta-, and eta-cyanocarboxylic acids in good yields. Furthermore, a series of gamma-keto acids also could be obtained by employing acyclic ketone oxime esters as the carbonyl radical precursor. It provides convergent access to diverse biologically important cyanocarboxylic and gamma-keto acids.
引用
收藏
页码:9654 / 9658
页数:5
相关论文
共 51 条
[1]  
Burns M. P., 2004, Patent No. 20041223
[2]  
Burns M. P., 2004, Patent No. [WO2004111256A1, 2004111256]
[3]   Discovery of phenoxybutanoic acid derivatives as potent endothelin antagonists with antihypertensive activity [J].
Cai, Jin ;
Liu, Ligang ;
Hong, Kwon Ho ;
Wang, Peng ;
Li, Lushen ;
Cao, Meng ;
Sun, Chunlong ;
Wu, Xiaoqing ;
Zong, Xi ;
Chen, Junqing ;
Ji, Min .
BIOORGANIC & MEDICINAL CHEMISTRY, 2015, 23 (04) :657-667
[4]   Photoinduced Copper-Catalyzed Asymmetric C-O Cross-Coupling [J].
Chen, Jun ;
Liang, Yu-Jie ;
Wang, Peng-Zi ;
Li, Guo-Qing ;
Zhang, Bin ;
Qian, Hao ;
Huan, Xiao-Die ;
Guan, Wei ;
Xiao, Wen-Jing ;
Chen, Jia-Rong .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2021, 143 (33) :13382-13392
[5]   Enantioselective Radical Ring-Opening Cyanation of Oxime Esters by Dual Photoredox and Copper Catalysis [J].
Chen, Jun ;
Wang, Peng-Zi ;
Lu, Bin ;
Liang, Dong ;
Yu, Xiao-Ye ;
Xiao, Wen-Jing ;
Chen, Jia-Rong .
ORGANIC LETTERS, 2019, 21 (23) :9763-9768
[6]   Transformation of Carbon Dioxide with Homogeneous Transition-Metal Catalysts: A Molecular Solution to a Global Challenge? [J].
Cokoja, Mirza ;
Bruckmeier, Christian ;
Rieger, Bernhard ;
Herrmann, Wolfgang A. ;
Kuehn, Fritz E. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (37) :8510-8537
[7]   Copper-Catalyzed Hydrocarboxylation of Alkynes Using Carbon Dioxide and Hydrosilanes [J].
Fujihara, Tetsuaki ;
Xu, Tinghua ;
Semba, Kazuhiko ;
Terao, Jun ;
Tsuji, Yasushi .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (02) :523-527
[8]  
He X, 2020, GREEN CHEM, V22, P7301, DOI [10.1039/D0GC02743J, 10.1039/d0gc02743j]
[9]   C-H Bond Carboxylation with Carbon Dioxide [J].
Hong, Junting ;
Li, Man ;
Zhang, Jianning ;
Sun, Beiqi ;
Mo, Fanyang .
CHEMSUSCHEM, 2019, 12 (01) :6-39
[10]   Visible-Light Photoredox-Catalyzed Ring-Opening Carboxylation of Cyclic Oxime Esters with CO2 [J].
Jiang, Yuan-Xu ;
Chen, Liang ;
Ran, Chuan-Kun ;
Song, Lei ;
Zhang, Wei ;
Liao, Li-Li ;
Yu, Da-Gang .
CHEMSUSCHEM, 2020, 13 (23) :6312-6317