Visible Light Photoredox Catalysis with Transition Metal Complexes: Applications in Organic Synthesis

被引:7609
作者
Prier, Christopher K. [1 ]
Rankic, Danica A. [1 ]
MacMillan, David W. C. [1 ]
机构
[1] Princeton Univ, Merck Ctr Catalysis, Princeton, NJ 08544 USA
关键词
PHOTOINDUCED ELECTRON-TRANSFER; C-H FUNCTIONALIZATION; REDOX-PHOTOSENSITIZED REACTIONS; HYDROGEN-ATOM ABSTRACTION; ALPHA-AMINOALKYL RADICALS; KETENE SILYL ACETALS; AMINE ALPHA; BETA-UNSATURATED KETONE; CONJUGATED CYCLOPROPYL KETONES; MULTIELECTRON CHARGE RELAYS; BOND-DISSOCIATION ENERGIES;
D O I
10.1021/cr300503r
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The chemical review highlights the early work on the use of transition metal complexes as photoredox catalysts to promote reactions of organic compounds. Studies on the use of transition metal complexes as visible light photocatalysts for organic synthesis have significantly benefited from advances in the related fields of organic and semiconductor photocatalysis. It is better to consider the photochemistry of the prototypical photoredox catalyst Ru(bpy)2+3 before discussing organic transformations enabled by photoredox catalysis. An electron in one of the photocatalyst's metal-centered t2g orbitals is excited to a ligand-centered π* orbital on absorption of a photon in the visible region. This transition is termed a metal to ligand charge transfer (MLCT) and results in a species in which the metal has been effectively oxidized to a Ru(III) oxidation state and the ligand framework has undergone a single-electron reduction.
引用
收藏
页码:5322 / 5363
页数:42
相关论文
共 292 条
[51]   Photocatalysis for the formation of the C-C bond [J].
Fagnoni, Maurizio ;
Dondi, Daniele ;
Ravelli, Davide ;
Albini, Angelo .
CHEMICAL REVIEWS, 2007, 107 (06) :2725-2756
[52]   Scope, limitations and mechanistic aspects of the photo-induced cross-linking of proteins by water-soluble metal complexes [J].
Fancy, DA ;
Denison, C ;
Kim, K ;
Xie, YQ ;
Holdeman, T ;
Amini, F ;
Kodadek, T .
CHEMISTRY & BIOLOGY, 2000, 7 (09) :697-708
[53]   Chemistry for the analysis of protein-protein interactions: Rapid and efficient cross-linking triggered by long wavelength light [J].
Fancy, DA ;
Kodadek, T .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1999, 96 (11) :6020-6024
[54]   Efficient electrocatalytic intramolecular anion radical cyclobutanation reactions [J].
Felton, GAN ;
Bauld, NL .
TETRAHEDRON, 2004, 60 (48) :10999-11010
[55]   Dramatic effects of the electrolyte cation on the selectivity of electroreductive cycloaddition reactions of bis(enones) [J].
Felton, GAN ;
Bauld, NL .
TETRAHEDRON LETTERS, 2004, 45 (46) :8465-8469
[56]   Photochemistry and photophysics of coordination compounds: Iridium [J].
Flamigni, Lucia ;
Barbieri, Andrea ;
Sabatini, Cristiana ;
Ventura, Barbara ;
Barigelletti, Francesco .
PHOTOCHEMISTRY AND PHOTOPHYSICS OF COORDINATION COMPOUNDS II, 2007, 281 :143-203
[57]   Control of a Living Radical Polymerization of Methacrylates by Light [J].
Fors, Brett P. ;
Hawker, Craig J. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (35) :8850-8853
[58]   Functionally Diverse Nucleophilic Trapping of Iminium Intermediates Generated Utilizing Visible Light [J].
Freeman, David B. ;
Furst, Laura ;
Condie, Allison G. ;
Stephenson, Corey R. J. .
ORGANIC LETTERS, 2012, 14 (01) :94-97
[59]   Selective trifluoromethylation and alkynylation of tetrahydroisoquinolines using visible light irradiation by Rose Bengal [J].
Fu, Weijun ;
Guo, Wenbo ;
Zou, Guanglong ;
Xu, Chen .
JOURNAL OF FLUORINE CHEMISTRY, 2012, 140 :88-94
[60]   Preference of electron transfer to nucleophilic addition in reactions of ketene silyl acetals with quinones and catalysis of magnesium ion [J].
Fujita, M ;
Fukuzumi, S ;
Matsubayashi, GE ;
Otera, J .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1996, 69 (04) :1107-1116