Cyclization-endoperoxidation cascade reactions of dienes mediated by a pyrylium photoredox catalyst

被引:40
作者
Gesmundo, Nathan J. [1 ]
Nicewicz, David A. [1 ]
机构
[1] Univ N Carolina, Dept Chem, Chapel Hill, NC 27599 USA
关键词
alkene; cascade; endoperoxide; oxidation; photoredox catalysis; ELECTRON; PEROXIDES; CYCLOADDITION; DERIVATIVES; ALKENES; SYSTEM; AGENTS; FUNGUS;
D O I
10.3762/bjoc.10.128
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Triarylpyrylium salts were employed as single electron photooxidants to catalyze a cyclization-endoperoxidation cascade of dienes. The transformation is presumed to proceed via the intermediacy of diene cation radicals. The nature of the diene component was investigated in this context to determine the structural requirements necessary for successful reactivity. Several unique endoperoxide structures were synthesized in yields up to 79%.
引用
收藏
页码:1272 / 1281
页数:10
相关论文
共 29 条
[1]  
Adam W., 1992, CRC HDB ORGANIC PHOT
[2]   Sesquiterpene constituents from the essential oil of the liverwort Plagiochila asplenioides [J].
Adio, AM ;
König, WA .
PHYTOCHEMISTRY, 2005, 66 (05) :599-609
[3]  
Ando W., 1992, Organic peroxides
[4]  
[Anonymous], 2013, GAUSS 09 REV D 01
[5]  
[Anonymous], J CHEM SOC REV
[6]  
BLOODWORTH AJ, 1985, SINGLET OXYGEN, V2
[7]   Antiangiogenic Effect of Chamigrane Endoperoxides from a Thai Mangrove-Derived Fungus [J].
Chokpaiboon, Supichar ;
Sommit, Damrong ;
Bunyapaiboonsri, Taridaporn ;
Matsubara, Kiminori ;
Pudhom, Khanitha .
JOURNAL OF NATURAL PRODUCTS, 2011, 74 (10) :2290-2294
[8]   Bioactive peroxides as potential therapeutic agents [J].
Dembitsky, Valery M. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2008, 43 (02) :223-251
[9]   Selective photocatalytic reactions with organic photocatalysts [J].
Fukuzumi, Shunichi ;
Ohkubo, Kei .
CHEMICAL SCIENCE, 2013, 4 (02) :561-574
[10]   Direct Catalytic Anti-Markovnikov Hydroetherification of Alkenols [J].
Hamilton, David S. ;
Nicewicz, David A. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (45) :18577-18580