Novel Oxidative Ugi Reaction for the Synthesis of Highly Active, Visible-Light, Imide-Acridinium Organophotocatalysts

被引:35
作者
Gini, Andrea [2 ]
Uygur, Mustafa [1 ]
Rigotti, Thomas [3 ]
Aleman, Jose [3 ,4 ]
Mancheno, Olga Garcia [1 ,2 ]
机构
[1] Univ Munster, Organ Chem Inst, D-48149 Munster, Germany
[2] Univ Regensburg, Organ Chem Inst, D-93053 Regensburg, Germany
[3] Univ Autonoma Madrid, Organ Chem Dept, Modulo 1, E-28049 Madrid, Spain
[4] Univ Autonoma Madrid, Inst Adv Res Chem Sci IAdChem, E-28049 Madrid, Spain
关键词
acridinium salts; C-H functionalization; multicomponent reactions; oxidation; photocatalysis; H BOND FUNCTIONALIZATION; PHOTOINDUCED ELECTRON-TRANSFER; PHOTOREDOX CATALYSIS; MOLECULAR-OXYGEN; RING EXPANSION; ION; PHOTOCATALYSIS; SALTS; STATE; ACID;
D O I
10.1002/chem.201802830
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A newly designed class of acridinium-based organophotocatalysts bearing an imide group at the C9-position is presented. To achieve these unprecedented structures, a synthetic strategy based on a novel straightforward oxidative Ugi-type reaction at the benzylic position of C9-unsubstituted acridanes was developed. The introduction of the imide-unit affords a notable photocatalytic activity enhancement, allowing efficient transformations in different oxidative and reductive visible-light catalytic reactions.
引用
收藏
页码:12509 / 12514
页数:6
相关论文
共 51 条
[1]  
Aleman J., 2015, RECENT ADV UGI MULTI, P245
[2]  
[Anonymous], 2011, ANGEW CHEM, DOI DOI 10.1021/jacs.5b05903
[3]  
Baeyer A., 1871, Ber. Dtsch. Chem. Ges, V4, P555, DOI DOI 10.1002/CBER.18710040209
[4]   Charge shift and triplet state formation in the 9-mesityl-10-methylacridinium cation [J].
Benniston, AC ;
Harriman, A ;
Li, PY ;
Rostron, JP ;
van Ramesdonk, HJ ;
Groeneveld, MM ;
Zhang, H ;
Verhoeven, JW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (46) :16054-16064
[5]  
Bockman TM, 1997, J PHYS ORG CHEM, V10, P542
[6]   Simultaneous Quantification of Multiple Nucleic Acid Targets Using Chemiluminescent Probes [J].
Browne, Kenneth A. ;
Deheyn, Dimitri D. ;
El-Hiti, Gamal A. ;
Smith, Keith ;
Weeks, Ian .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (37) :14637-14648
[7]   Visible-Light Photoredox Catalyzed Three-Component Cyclization of 2H-Azirines, Alkynyl Bromides, and Molecular Oxygen to Oxazole Skeleton [J].
Chen, Lili ;
Li, Hongji ;
Li, Pinhua ;
Wang, Lei .
ORGANIC LETTERS, 2016, 18 (15) :3646-3649
[8]   Visible light mediated sp3 C-H bond functionalization of N-aryl-1,2,3,4-tetrahydroisoquinolines via Ugi-type three-component reaction [J].
Chen, Yunyun ;
Feng, Gaofeng .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (14) :4260-4265
[9]   Introduction: CH Activation [J].
Crabtree, Robert H. ;
Lei, Aiwen .
CHEMICAL REVIEWS, 2017, 117 (13) :8481-+
[10]   IBX-mediated oxidation of unactivated cyclic amines: application in highly diastereoselective oxidative Ugi-type and aza-Friedel-Crafts reactions [J].
de Graaff, C. ;
Bensch, L. ;
van Lint, Matthijs J. ;
Ruijter, E. ;
Orru, R. V. A. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (40) :10108-10112