Aerobic organocatalytic photoinitiated arene oxidations: Application to electron transfer initiated cyclization reactions

被引:23
作者
Kumar, VS [1 ]
Aubele, DL [1 ]
Floreancig, PE [1 ]
机构
[1] Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA
关键词
D O I
10.1021/ol016996f
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] Electron transfer initiated oxidative cyclization reactions can be effected by catalytic amounts of N-methylquinolinium hexafluorophosphate through photoirradiation in the presence of dioxygen. Solid sodium thiosulfate serves as an effective reducing agent to remove the reactive oxygen species formed from catalyst regeneration and radical coupling reactions with O-2, allowing these cyclizations to proceed efficiently on preparatively useful scales.
引用
收藏
页码:4123 / 4125
页数:3
相关论文
共 25 条
[1]  
BACKVALL JE, 1990, J AM CHEM SOC, V112, P5160
[2]  
Barton D.H.R, 1993, ACTIVATION DIOXYGEN
[3]   Gif chemistry: The present situation [J].
Barton, DHR .
TETRAHEDRON, 1998, 54 (22) :5805-5817
[4]   Aerobic oxidations of conjugated dienes using a catalytic palladium(II)-quinone-heteropolyacid system for electron transfer from organic substrates to molecular oxygen [J].
Bergstad, K ;
Grennberg, H ;
Backvall, JE .
ORGANOMETALLICS, 1998, 17 (01) :45-50
[5]   Efficient and selective aerobic oxidation of alcohols into aldehydes and ketones using ruthenium/TEMPO as the catalytic system [J].
Dijksman, A ;
Marino-González, A ;
Payeras, AMI ;
Arends, IWCE ;
Sheldon, RA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (28) :6826-6833
[6]   Osmium-catalyzed dihydroxylation of olefins using dioxygen or air as the terminal oxidant [J].
Döbler, C ;
Mehltretter, GM ;
Sundermeier, U ;
Beller, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (42) :10289-10297
[7]   Nucleophile-assisted cleavage of benzyltrialkylsilane cation radicals [J].
Dockery, KP ;
Dinnocenzo, JP ;
Farid, S ;
Goodman, JL ;
Gould, IR ;
Todd, WP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (08) :1876-1883
[8]   Synthesis of axially chiral N-hydroxyimides, potential new catalysts for asymmetric oxidations [J].
Einhorn, C ;
Einhorn, J ;
Marcadal-Abbadi, C ;
Pierre, JL .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (12) :4542-4546
[9]   Addition versus oxygenation of alkylbenzenes with 10-methylacridinium ion via photoinduced electron transfer [J].
Fujita, M ;
Ishida, A ;
Takamuku, S ;
Fukuzumi, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (36) :8566-8574
[10]   Photoalkylation of 10-alkylacridinium ion via a charge-shift type of photoinduced electron transfer controlled by solvent polarity [J].
Fukuzumi, S ;
Ohkubo, K ;
Suenobu, T ;
Kato, K ;
Fujitsuka, M ;
Ito, O .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (35) :8459-8467