Vilsmeier-Haack reagent mediated synthetic transformations with an immobilized iridium complex photoredox catalyst

被引:22
作者
Zhi, Peng [1 ]
Xi, Zi-Wei [1 ]
Wang, Dan-Yan [2 ]
Wang, Wei [3 ]
Liang, Xue-Zheng [1 ]
Tao, Fei-Fei [1 ]
Shen, Run-Pu [1 ]
Shen, Yong-Miao [1 ,2 ]
机构
[1] Shaoxing Univ, Sch Chem & Chem Engn, Key Lab Clean Dyeing & Finishing Technol Zhejiang, Shaoxing 312000, Peoples R China
[2] Zhejiang Sci Tech Univ, Dept Chem, Hangzhou 310018, Zhejiang, Peoples R China
[3] Shaoxing Univ, Sch Civil Engn, Shaoxing 312000, Peoples R China
基金
中国国家自然科学基金; 中国博士后科学基金;
关键词
PHOTOCATALYTIC APPROACH; TERTIARY ANILINES; TITANIUM-DIOXIDE; ROOM-TEMPERATURE; IONIC LIQUIDS; REARRANGEMENT; FORMYLATION; CYCLIZATION; ANHYDRIDES; DRIVEN;
D O I
10.1039/c8nj05288c
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An immobilized iridium complex photocatalyst Ir(ppy)(2)(PDVB-py) was synthesized by immobilization of the iridium complex onto the nanoporous vinylpyridine-divinylbenzene copolymer (PDVB-py). Its application for the synthesis of amides, nitriles, and anhydrides was reported via reactions under the action of the visible-light-driven in situ generated Vilsmeier-Haack reagent from CBr4 in DMF. The results showed that this heterogeneous photocatalyst has extremely high activity and excellent stability to be recycled five times.
引用
收藏
页码:709 / 717
页数:9
相关论文
共 84 条
[1]   Metal-Free Multicomponent Syntheses of Pyridines [J].
Allais, Christophe ;
Grassot, Jean-Marie ;
Rodriguez, Jean ;
Constantieux, Thierry .
CHEMICAL REVIEWS, 2014, 114 (21) :10829-10868
[2]   Visible Light Mediated Aryl Migration by Homolytic C-N Cleavage of Aryl Amines [J].
Alpers, Dirk ;
Cole, Kevin P. ;
Stephenson, Corey R. J. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (37) :12167-12170
[3]   Metallaphotoredox Difluoromethylation of Aryl Bromides [J].
Bacauanu, Vlad ;
Cardinal, Sebastien ;
Yamauchi, Motoshi ;
Kondo, Masaru ;
Fernandez, David F. ;
Remy, Richard ;
MacMillan, David W. C. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (38) :12543-12548
[4]   Design, synthesis and characterization of new 1,2,3-triazolyl pyrazole derivatives as potential antimicrobial agents via a Vilsmeier-Haack reaction approach [J].
Bhat, Manjunatha ;
Nagaraja, G. K. ;
Kayarmar, Reshma ;
Peethamber, S. K. ;
Shafeeulla, Mohammed R. .
RSC ADVANCES, 2016, 6 (64) :59375-59388
[5]  
Buzzetti L., 2017, ANGEW CHEMIE, V129, P15235
[6]   Heterogeneous Visible-Light Photoredox Catalysis with Graphitic Carbon Nitride for α-Aminoalkyl Radical Additions, Allylations, and Heteroarylations [J].
Cai, Yunfei ;
Tang, Yurong ;
Fan, Lulu ;
Lefebvre, Quentin ;
Hou, Hong ;
Rueping, Magnus .
ACS CATALYSIS, 2018, 8 (10) :9471-+
[7]   Visible light photoredox-controlled reactions of N-radicals and radical ions [J].
Chen, Jia-Rong ;
Hu, Xiao-Qiang ;
Lu, Liang-Qiu ;
Xiao, Wen-Jing .
CHEMICAL SOCIETY REVIEWS, 2016, 45 (08) :2044-2056
[8]   Relay photocatalytic cascade reactions: synthesis of indolo[2,1-a] isoquinoline derivatives via double C(sp3)-H bond functionalization [J].
Cheng, Jian ;
Xie, Jin ;
Zhu, Chengjian .
CHEMICAL COMMUNICATIONS, 2018, 54 (13) :1655-1658
[9]   DIAZAINDENES (AZAINDOLES) .3. REACTIONS OF VILSMEIER REAGENTS LEADING TO 3-FORMYL-1,6-DIAZAINDENE AND -1,4-DIAZABENZ[F]INDENE [J].
CLARK, BAJ ;
PARRICK, J ;
WEST, PJ ;
KELLY, AH .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1970, (03) :498-+
[10]   Visible-light-mediated conversion of alcohols to halides [J].
Dai, Chunhui ;
Narayanam, Jagan M. R. ;
Stephenson, Corey R. J. .
NATURE CHEMISTRY, 2011, 3 (02) :140-145