Synthesis of Z-alkenes via visible light promoted photocatalytic E → Z isomerization under metal-free conditions

被引:71
作者
Cai, Wenbin [1 ]
Fan, Huaqiang [1 ]
Ding, Dazhong [2 ]
Zhang, Yongqiang [1 ]
Wang, Wei [1 ,3 ]
机构
[1] East China Univ Sci & Technol, Sch Pharm, Shanghai 200237, Peoples R China
[2] Qingdao Inst Food & Drug Control, Qingdao 266000, Peoples R China
[3] Univ New Mexico, Dept Chem & Chem Biol, Albuquerque, NM 87131 USA
关键词
PHOTOCHEMICAL-REACTIONS; ENERGY-TRANSFER; MECHANISMS; OLEFIN; METATHESIS; ACTIVATION; CATALYSTS; RING;
D O I
10.1039/c7cc07984b
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A green approach for the synthesis of thermodynamically less stable Z-alkenes has been presented through the exploration of visible light promoted photocatalytic E-to-Z isomerization. This protocol features metal-free conditions, which is operationally simple, remarkably clean, and allows the synthesis of both electron-rich and electron-deficient Z-alkenes with diverse functional groups.
引用
收藏
页码:12918 / 12921
页数:4
相关论文
共 32 条
[1]   NOVEL PHOTOINDUCED HYDROGEN-ATOM TRANSFER THROUGH INTRAMOLECULAR HYDROGEN-BONDING COUPLED WITH CIS-TRANS ISOMERIZATION IN CIS-1-(2-PYRROLYL)-2-(2-QUINOLYL)ETHENE [J].
ARAI, T ;
MORIYAMA, M ;
TOKUMARU, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (07) :3171-3172
[2]   PHOTOCHEMICAL ONE-WAY ADIABATIC ISOMERIZATION OF AROMATIC OLEFINS [J].
ARAI, T ;
TOKUMARU, K .
CHEMICAL REVIEWS, 1993, 93 (01) :23-39
[3]   CONTROL OF STERIC COURSE OF WITTIG REACTION - STEREOCHEMICAL STUDIES AND SYNTHETIC APPLICATIONS [J].
BERGELSON, LD ;
SHEMYAKIN, MM .
TETRAHEDRON, 1963, 19 (01) :149-&
[4]   Photochemical E (trans) → Z (cis) isomerization in substituted 1-naphthylacrylates [J].
Bushan, KM ;
Rao, GV ;
Soujanya, T ;
Rao, VJ ;
Saha, S ;
Samanta, A .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (03) :681-688
[5]   Chelated Ruthenium Catalysts for Z-Selective Olefin Metathesis [J].
Endo, Koji ;
Grubbs, Robert H. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (22) :8525-8527
[6]   Immobilization and Continuous Recycling of Photoredox Catalysts in Ionic Liquids for Applications in Batch Reactions and Flow Systems: Catalytic Alkene Isomerization by Using Visible Light [J].
Fabry, David C. ;
Ronge, Meria A. ;
Rueping, Magnus .
CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (14) :5350-5354
[7]   The Multiple Mechanisms of Cell Death Triggered by Resveratrol in Lymphoma and Leukemia [J].
Frazzi, Raffaele ;
Tigano, Marco .
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, 2014, 15 (03) :4977-4993
[8]   MECHANISMS OF PHOTOREACTIONS IN SOLUTION .18. ENERGY TRANSFER WITH NONVERTICAL TRANSITIONS [J].
HAMMOND, GS ;
SALTIEL, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (16) :2516-&
[9]   MECHANISMS OF PHOTOCHEMICAL REACTIONS IN SOLUTION .22. PHOTOCHEMICAL CIS-TRANS ISOMERIZATION [J].
HAMMOND, GS ;
SALTIEL, J ;
BRADSHAW, JS ;
TURRO, NJ ;
LAMOLA, AA ;
VOGT, V ;
COUNSELL, RC ;
COWAN, DO ;
DALTON, C .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (16) :3197-&
[10]   MECHANISMS OF PHOTOCHEMICAL REACTIONS IN SOLUTION .39. STUDY OF ENERGY TRANSFER BY KINETIC SPECTROPHOTOMETRY [J].
HERKSTRO.WG ;
HAMMOND, GS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (21) :4769-&