Visible-light photocatalytic oxidation of 1,3-dicarbonyl compounds and carbon-carbon bond formation

被引:30
作者
Daniel, Marion [1 ,2 ]
Fensterbank, Louis [1 ,2 ]
Goddard, Jean-Philippe [1 ,2 ,3 ]
Ollivier, Cyril [1 ,2 ]
机构
[1] Univ Paris 06, Sorbonne Univ, Inst Parisien Chim Mol, UMR 8232, F-75005 Paris, France
[2] CNRS, UMR 8232, Inst Parisien Chim Mol, F-75005 Paris, France
[3] Univ Haute Alsace, Lab Chim Organ & Bioorgan, Ecole Natl Super Chim Mulhouse, EA 4566, F-68093 Mulhouse, France
来源
ORGANIC CHEMISTRY FRONTIERS | 2014年 / 1卷 / 05期
关键词
FREE-RADICAL CYCLIZATIONS; PHOTOREDOX CATALYSIS; ELECTRON-TRANSFER; FORMING REACTIONS; ORGANIC-SYNTHESIS; SYNTHETIC APPLICATIONS; PSCHORR REACTION; SULFONIUM SALTS; DIAZONIUM SALTS; EXCITED-STATES;
D O I
10.1039/c4qo00071d
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Visible-light photocatalytic oxidation of 1,3-dicarbonyl compounds, using Ru(bpy)(3)Cl-2 as a photocatalyst and combining molecular oxygen and triphenylcarbenium as a new sacrificial acceptor, has been developed for carbon-carbon bond formation giving access to dimerization, allylation and polycyclization products.
引用
收藏
页码:551 / 555
页数:5
相关论文
共 64 条
[51]   Manganese(III)-based oxidative free-radical cyclizations [J].
Snider, BB .
CHEMICAL REVIEWS, 1996, 96 (01) :339-363
[52]   PHOTOREDOX CATALYSIS BY [Ru(bpy)3]2+ TO TRIGGER TRANSFORMATIONS OF ORGANIC MOLECULES. ORGANIC SYNTHESIS USING VISIBLE-LIGHT PHOTOCATALYSIS AND ITS 20th CENTURY ROOTS [J].
Teply, Filip .
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 2011, 76 (07) :859-917
[53]   Shining Light on Photoredox Catalysis: Theory and Synthetic Applications [J].
Tucker, Joseph W. ;
Stephenson, Corey R. J. .
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (04) :1617-1622
[54]   CHEMISTRY OF DIHYDROPYRIDINES .9. HYDRIDE TRANSFER FROM 1,4-DIHYDROPYRIDINES TO SP3-HYBRIDIZED CARBON IN SULFONIUM SALTS AND ACTIVATED HALIDES - STUDIES WITH NAD(P)H MODELS [J].
VANBERGEN, TJ ;
HEDSTRAND, DM ;
KRUIZINGA, WH ;
KELLOGG, RM .
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (26) :4953-4962
[55]   Radical Carbon-Carbon Bond Formations Enabled by Visible Light Active Photocatalysts [J].
Wallentin, Carl-Johan ;
Nguyen, John D. ;
Stephenson, Corey R. J. .
CHIMIA, 2012, 66 (06) :394-398
[56]   Synthetic applications of photoredox catalysis with visible light [J].
Xi, Yumeng ;
Yi, Hong ;
Lei, Aiwen .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (15) :2387-2403
[57]   When C-H bond functionalization meets visible-light photoredox catalysis [J].
Xie, Jin ;
Jin, Hongming ;
Xu, Pan ;
Zhu, Chengjian .
TETRAHEDRON LETTERS, 2014, 55 (01) :36-48
[58]   Practical Metal- Free C( sp3)-H Functionalization: Construction of Structurally Diverse a- Substituted N- Benzyl and N-Allyl Carbamates [J].
Xie, Zhiyu ;
Liu, Lei ;
Chen, Wenfang ;
Zheng, Hongbo ;
Xu, Qingqing ;
Yuan, Huiqing ;
Lou, Hongxiang .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (15) :3904-3908
[59]   Visible-Light-Driven Photoredox Catalysis in the Construction of Carbocyclic and Heterocyclic Ring Systems [J].
Xuan, Jun ;
Lu, Liang-Qiu ;
Chen, Jia-Rong ;
Xiao, Wen-Jing .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (30) :6755-6770
[60]   Visible-Light Photoredox Catalysis [J].
Xuan, Jun ;
Xiao, Wen-Jing .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (28) :6828-6838