Iminyl Radical-Triggered 1,5-Hydrogen-Atom Transfer/Heck-Type Coupling by Visible-Light Photoredox Catalysis

被引:30
作者
Chen, Li [1 ,2 ]
Guo, Li-Na [1 ,2 ]
Ma, Zhi-Yong [1 ,2 ]
Gu, Yu-Rui [1 ,2 ]
Zhang, Junjie [1 ,2 ]
Duan, Xin-Hua [1 ,2 ]
机构
[1] Xi An Jiao Tong Univ, Dept Chem, Sch Sci, Xian Key Lab Sustainable Energy Mat Chem, Xian 710049, Shaanxi, Peoples R China
[2] Xi An Jiao Tong Univ, MOE Key Lab Nonequilibrium Synth & Modulat Conden, Xian 710049, Shaanxi, Peoples R China
基金
中国国家自然科学基金;
关键词
INTRAMOLECULAR HYDROGEN ABSTRACTION; C-H FUNCTIONALIZATION; OXIME ESTERS; BOND; STRATEGY; OLEFINATION; GENERATION; ALKENES; CASCADE; HECK;
D O I
10.1021/acs.joc.9b00525
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient iminyl radical-triggered 1,5-hydrogen-atom transfer/Heck-type coupling cascade has been achieved through visible-light photoredox catalysis. A variety of unactivated C(sp(3))-H bonds have been alkenylated efficiently and selectively with easily available alkenes, providing an elegant route to gamma-alkenylated ketone.
引用
收藏
页码:6475 / 6482
页数:8
相关论文
共 59 条
[1]   The heck reaction as a sharpening stone of palladium catalysis [J].
Beletskaya, IP ;
Cheprakov, AV .
CHEMICAL REVIEWS, 2000, 100 (08) :3009-3066
[2]   IMINYL RADICALS .2. RING-OPENING OF CYCLOBUTYL- AND CYCLOPENTYLIMINYL RADICALS [J].
BOIVIN, J ;
FOUQUET, E ;
ZARD, SZ .
TETRAHEDRON, 1994, 50 (06) :1757-1768
[3]   IMINYL RADICALS .1. GENERATION AND INTRAMOLECULAR CAPTURE BY AN OLEFIN [J].
BOIVIN, J ;
FOUQUET, E ;
ZARD, SZ .
TETRAHEDRON, 1994, 50 (06) :1745-1756
[4]   IMINYL RADICALS .3. FURTHER SYNTHETICALLY USEFUL SOURCES OF IMINYL RADICALS [J].
BOIVIN, J ;
FOUQUET, E ;
SCHIANO, AM ;
ZARD, SZ .
TETRAHEDRON, 1994, 50 (06) :1769-1776
[5]   Metal-Involving Synthesis and Reactions of Oximes [J].
Bolotin, Dmitrii S. ;
Bokach, Nadezhda A. ;
Demakova, Marina Ya. ;
Kukushkin, Vadim Yu. .
CHEMICAL REVIEWS, 2017, 117 (21) :13039-13122
[6]   The modern interpretation of the Wittig reaction mechanism [J].
Byrne, Peter A. ;
Gilheany, Declan G. .
CHEMICAL SOCIETY REVIEWS, 2013, 42 (16) :6670-6696
[7]   sp3 C-H oxidation by remote H-radical shift with oxygen- and nitrogen-radicals: a recent update [J].
Chiba, Shunsuke ;
Chen, Hui .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (24) :4051-4060
[8]   Complementary Strategies for Directed C(sp3)-H Functionalization: A Comparison of Transition-Metal-Catalyzed Activation, Hydrogen Atom Transfer, and Carbene/Nitrene Transfer [J].
Chu, John C. K. ;
Rovis, Tomislav .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (01) :62-101
[9]   Mn-, Fe-, and Co-Catalyzed Radical Hydrofunctionalizations of Olefins [J].
Crossley, Steven W. M. ;
Obradors, Carla ;
Martinez, Ruben M. ;
Shenvi, Ryan A. .
CHEMICAL REVIEWS, 2016, 116 (15) :8912-9000
[10]   Photoinduced Remote Functionalisations by Iminyl Radical Promoted C-C and C-H Bond Cleavage Cascades [J].
Dauncey, Elizabeth M. ;
Morcillo, Sara P. ;
Douglas, James J. ;
Sheikh, Nadeem S. ;
Leonori, Daniele .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (03) :744-748