Photoorganocatalysis. What for?

被引:801
作者
Ravelli, Davide [1 ]
Fagnoni, Maurizio [1 ]
Albini, Angelo [1 ]
机构
[1] Univ Pavia, Dept Chem, PhotoGreen Lab, I-27100 Pavia, Italy
关键词
PHOTOCHEMICALLY INDUCED ADDITION; VISIBLE-LIGHT PHOTOCATALYSIS; ELECTRON-DEFICIENT ALKENES; GRAPHITIC CARBON NITRIDE; TERTIARY-AMINES; METAL-FREE; PHOTOREDOX CATALYSIS; RADICAL-ADDITION; ALPHA-ENONES; SYNTHETIC APPLICATIONS;
D O I
10.1039/c2cs35250h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
In the reactions reviewed, an organic molecule under irradiation catalyzes a chemical reaction. The activation is based either on hydrogen or on electron transfer. Commonly used photoorganocatalysts are aromatic ketones, quinones, heterocycles, dyes; intermediates formed are radicals, radical ions and ions from precursors such as alkanes, alkenes, amines, ethers etc. Oxidation (mainly oxygenation) and reduction processes are obtained along with the alpha-functionalization of amines and ketones, conjugate additions, cycloadditions etc. The key characteristic of the method is the smooth generation of highly reactive intermediates under mild conditions.
引用
收藏
页码:97 / 113
页数:17
相关论文
共 96 条
[1]   Photosensitized intramolecular cyclization of furan and non-activated alkene: pathway switching by the substituent on the furan ring [J].
Arai, Noriyoshi ;
Tanaka, Koichiro ;
Ohkuma, Takeshi .
TETRAHEDRON LETTERS, 2010, 51 (09) :1273-1275
[2]   Novel [4+2] cycloaddition between thiobenzophenone and aryl-substituted alkenes via photoinduced electron transfer [J].
Arguello, Juan E. ;
Perez-Ruiz, Raul ;
Miranda, Miguel A. .
ORGANIC LETTERS, 2007, 9 (18) :3587-3590
[3]   Catalytic enantioselective reactions driven by photoinduced electron transfer [J].
Bauer, A ;
Westkämper, F ;
Grimme, S ;
Bach, T .
NATURE, 2005, 436 (7054) :1139-1140
[4]  
Beller M., 2004, TRANSITION METALS OR
[5]   CONJUGATE ADDITION OF METHANOL TO ALPHA-ENONES - PHOTOCHEMISTRY AND STEREOCHEMICAL DETAILS [J].
BENKO, Z ;
FRASERREID, B ;
MARIANO, PS ;
BECKWITH, ALJ .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (09) :2066-2072
[6]  
Berkessel A, 2005, ASYMMETRIC ORGANOCATALYSIS: FROM BIOMIMETIC CONCEPTS TO APPLICATIONS IN ASYMMETRIC SYNTHESIS, P1, DOI 10.1002/3527604677
[7]   Stereoselective radical addition of tertiary amines to (5R)-5-menthyloxy-2[5H]-furanone:: Application to the enantioselective synthesis of (-)-isoretronecanol and (+)-laburnine [J].
Bertrand, S ;
Hoffmann, N ;
Pete, JP .
TETRAHEDRON LETTERS, 1999, 40 (16) :3173-3174
[8]   Diastereoselective tandem addition-cyclization reactions of unsaturated tertiary amines initiated by photochemical electron transfer (PET) [J].
Bertrand, S ;
Hoffmann, N ;
Humbel, S ;
Pete, JP .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (25) :8690-8703
[9]   Highly efficient photochemical addition of tertiary amines to electron deficient alkenes.: Diastereoselective addition to (5R)-5-Menthyloxy-2[5H]-furanone [J].
Bertrand, S ;
Glapski, C ;
Hoffmann, N ;
Pete, JP .
TETRAHEDRON LETTERS, 1999, 40 (16) :3169-3172
[10]   Photocatalytic oxidation of aliphatic and aromatic sulfides in the presence of silica adsorbed or zeolite-encapsulated 2,4,6-triphenyl(thia)pyrylium [J].
Bonesi, Sergio M. ;
Carbonell, Esther ;
Garcia, Hermenegildo ;
Fagnoni, Maurizio ;
Albini, Angelo .
APPLIED CATALYSIS B-ENVIRONMENTAL, 2008, 79 (04) :368-375