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
[11]   Hydroxylamine Derivatives as Nitrogen-Radical Precursors in Visible-Light Photochemistry [J].
Davies, Jacob ;
Morcillo, Sara P. ;
Douglas, James J. ;
Leonori, Daniele .
CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (47) :12154-12163
[12]   Transition-Metal-Catalyzed C-H Alkylation Using Alkenes [J].
Dong, Zhe ;
Ren, Zhi ;
Thompson, Samuel J. ;
Xu, Yan ;
Dong, Guangbin .
CHEMICAL REVIEWS, 2017, 117 (13) :9333-9403
[13]   Palladium-catalyzed alternating copolymerization of alkenes and carbon monoxide [J].
Drent, E ;
Budzelaar, PHM .
CHEMICAL REVIEWS, 1996, 96 (02) :663-681
[14]   Stereocontrolled synthesis of tetrasubstituted olefins [J].
Flynn, Alison B. ;
Ogilvie, William W. .
CHEMICAL REVIEWS, 2007, 107 (11) :4698-4745
[15]   IMINYLS .7. INTRAMOLECULAR HYDROGEN ABSTRACTION - SYNTHESIS OF HETEROCYCLIC-ANALOGS OF ALPHA-TETRALONE [J].
FORRESTER, AR ;
NAPIER, RJ ;
THOMSON, RH .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (03) :984-987
[16]   IMINYLS .5. INTRA-MOLECULAR HYDROGEN ABSTRACTION BY ALKYL(ARYL)-IMINYLS - NEW TETRALONE SYNTHESIS [J].
FORRESTER, AR ;
GILL, M ;
NAPIER, RJ ;
THOMSON, RH .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1979, (03) :632-636
[17]  
FORRESTER AR, 1976, J CHEM SOC CHEM COMM, P677, DOI 10.1039/c39760000677
[18]   The Cross-Dehydrogenative Coupling of Csp3-H Bonds: A Versatile Strategy for C-C Bond Formations [J].
Girard, Simon A. ;
Knauber, Thomas ;
Li, Chao-Jun .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (01) :74-100
[19]   Iminyl Radical-Triggered Intermolecular Distal C(sp3)-H Heteroarylation via 1,5-Hydrogen-Atom Transfer (HAT) Cascade [J].
Gu, Yu-Rui ;
Duan, Xin-Hua ;
Chen, Li ;
Ma, Zhi-Yong ;
Gao, Pin ;
Guo, Li-Na .
ORGANIC LETTERS, 2019, 21 (04) :917-920
[20]   PALLADIUM-CATALYZED REACTIONS OF ORGANIC HALIDES WITH OLEFINS [J].
HECK, RF .
ACCOUNTS OF CHEMICAL RESEARCH, 1979, 12 (04) :146-151