Metal-Free, Room-Temperature, Radical Alkoxycarbonylation of Aryldiazonium Salts through Visible-Light Photoredox Catalysis

被引:171
作者
Guo, Wei [1 ]
Lu, Liang-Qiu [1 ]
Wang, Yue [1 ]
Wang, Ya-Ni [1 ]
Chen, Jia-Rong [1 ]
Xiao, Wen-Jing [1 ,2 ]
机构
[1] Cent China Normal Univ, Key Lab Pesticide & Chem Biol, Minist Educ, Coll Chem, Wuhan 430079, Hubei, Peoples R China
[2] Collaborat Innovat Ctr Chem Sci & Engn, Tianjin, Peoples R China
基金
美国国家科学基金会;
关键词
diazo compounds; esters; photocatalysis; radicals; synthetic methods; ATOM-TRANSFER CARBONYLATION; ARYL DIAZONIUM SALTS; C-H ARYLATION; ALKYL IODIDES; COUPLING REACTIONS; CARBON-MONOXIDE; SATURATED ALCOHOLS; DELTA-LACTONES; SEQUENCE; ALKENES;
D O I
10.1002/anie.201408837
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The first radical alkoxycarboxylation of aryldiazonium salts using CO gas through visible-light-induced photo-redox catalysis (16 W blue LEDs) has been developed. This reaction is entirely metal-free, is carried out at room temperature with a low loading of an organic dye as a photocatalyst (0.5 mol%), and provides a wide range of arylcarboxylic acid esters in high yields. Importantly, this photocatalytic system can be successfully extended to other carboxylation reactions.
引用
收藏
页码:2265 / 2269
页数:5
相关论文
共 54 条
[1]  
[Anonymous], MORDEN CARBOXYLATION
[2]  
[Anonymous], 2014, ANGEW CHEM-GER EDIT
[3]  
Beller M, 2006, TOP ORGANOMETAL CHEM, V18, P1, DOI 10.1007/b105253
[4]  
Beller M., 2004, Transition Metals for Organic Synthesis, V1
[5]   Palladium-Catalyzed Carbonylation Reactions of Aryl Halides and Related Compounds [J].
Brennfuehrer, Anne ;
Neumann, Helfried ;
Beller, Matthias .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (23) :4114-4133
[6]  
Brennfuhrer A., 2009, ANGEW CHEM, V121, P4176, DOI 10.1002/ange.200900013
[7]  
de Meijere A., 2004, METAL CATALYZED CROS
[8]   Recent advances in the Heck-Matsuda reaction in heterocyclic chemistry [J].
Felpin, Francois-Xavier ;
Nassar-Hardy, Luma ;
Le Callonnec, Francois ;
Fouquet, Eric .
TETRAHEDRON, 2011, 67 (16) :2815-2831
[9]   Effective acceleration of atom transfer carbonylation of alkyl iodides by metal complexes. Application to the synthesis of the hinokinin precursor and dihydrocapsaicin [J].
Fukuyama, T ;
Nishitani, S ;
Inouye, T ;
Morimoto, K ;
Ryu, I .
ORGANIC LETTERS, 2006, 8 (07) :1383-1386
[10]   Pd/Light-Accelerated Atom-Transfer Carbonylation of Alkyl Iodides: Applications in Multicomponent Coupling Processes Leading to Functionalized Carboxylic Acid Derivatives [J].
Fusano, Akira ;
Sumino, Shuhei ;
Nishitani, Satoshi ;
Inouye, Takaya ;
Morimoto, Keisuke ;
Fukuyama, Takahide ;
Ryu, Ilhyong .
CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (30) :9415-9422