Visible-Light-Driven Intermolecular Reductive Ene-Yne Coupling by Iridium/Cobalt Dual Catalysis for C(sp3)-C(sp2) Bond Formation

被引:19
作者
Gonzalez, Maria J. [1 ]
Breit, Bernhard [1 ]
机构
[1] Albert Ludwigs Univ Freiburg, Inst Organ Chem, Albertstr 21, D-79104 Freiburg, Germany
关键词
alkynes; cobalt; dual catalysis; photoredox; reductive coupling; PHOTOREDOX CATALYSIS; COBALT CATALYSIS; HANTZSCH ESTERS; CARBON-CARBON; ALKYNES; 4-ALKYL-1,4-DIHYDROPYRIDINES; CYCLIZATIONS; COMPLEXES; ALDEHYDES; REAGENTS;
D O I
10.1002/chem.201903708
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A new methodology to form C(sp(3))-C(sp(2)) bonds by visible-light-driven intermolecular reductive ene-yne coupling has been successfully developed. The process relies on the ability of the Hantzsch ester to contribute in both SET and HAT processes through a unified cobalt and iridium catalytic system. This procedure avoids the use of stoichiometric amounts of reducing metallic reagents, which is translated into high functional-group tolerance and atom economy.
引用
收藏
页码:15746 / 15750
页数:5
相关论文
共 62 条
[1]  
Albini A., 2010, Handbook of synthetic photochemistry
[2]  
[Anonymous], 1882, Ann. Chem., DOI DOI 10.1002/JLAC.18822150102
[3]  
[Anonymous], ANGEW CHEM
[4]  
[Anonymous], 2004, ANGEW CHEM
[5]   [2+2+2]CYCLOADDITIONS OF ALKYNES TO FURANS AND THIOPHENES - A COBALT-MEDIATED ENOL ETHER WALK [J].
BOESE, R ;
HARVEY, DF ;
MALASKA, MJ ;
VOLLHARDT, KPC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (24) :11153-11154
[6]   Cobalt-Catalyzed Cross-Coupling Reactions [J].
Cahiez, Gerard ;
Moyeux, Alban .
CHEMICAL REVIEWS, 2010, 110 (03) :1435-1462
[7]   Cobalt-catalyzed regioselective carbocyclization reaction of o-iodophenyl ketones and aldehydes with alkynes, acrylates, and acrylonitrile:: A facile route to indenols and indenes [J].
Chang, KJ ;
Rayabarapu, DK ;
Cheng, CH .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (14) :4781-4787
[8]   Building Congested Ketone: Substituted Hantzsch Ester and Nitrile as Alkylation Reagents in Photoredox Catalysis [J].
Chen, Wenxin ;
Liu, Zheng ;
Tian, Jiaqi ;
Li, Jin ;
Ma, Jing ;
Cheng, Xu ;
Li, Guigen .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (38) :12312-12315
[9]  
Coates R.M., 1999, Reagents, Auxiliaries and Catalysts for C-C bonds
[10]   Cobalt Catalysis in the Gas Phase: Experimental Characterization of Cobalt(I) Complexes as Intermediates in Regioselective Diels-Alder Reactions [J].
Fiebig, Lukas ;
Kuttner, Julian ;
Hilt, Gerhard ;
Schwarzer, Martin C. ;
Frenking, Gernot ;
Schmalz, Hans-Guenther ;
Schaefer, Mathias .
JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (20) :10485-10493