Ir(iii)-catalyzed thioether directed arene C-H alkenylation

被引:14
作者
Li, Chen [1 ]
Chen, Xian [1 ]
Bao, Rui-Peng [2 ]
Li, Dong-Li [1 ]
Zhang, Kun [1 ]
Wang, Dong-Hui [2 ]
机构
[1] Wuyi Univ, Sch Biotechnol & Hlth Sci, 22 Dangcheng Vill, Jiangmen 529020, Guangdong, Peoples R China
[2] Univ Chinese Acad Sci, Shanghai Inst Organ Chem, Ctr Excellence Mol Synth, CAS Key Lab Synthet & Self Assembly Chem Organ Fu, 345 Linngling Rd, Shanghai 200032, Peoples R China
基金
国家重点研发计划;
关键词
BENZYL THIOETHERS; SULFUR; FUNCTIONALIZATION; ARYLATION; ACTIVATION; SULFOXIDES; DERIVATIVES; OLEFINATION; AMIDATION;
D O I
10.1039/c9ra06811b
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
In this study, we demonstrate an Ir(iii)-catalyzed thioether directed alkenylation of arene C-H bonds under mild reaction conditions. The selectivity for mono- or di-alkenylation is controlled by the concentration of alkene and oxidant loading. Various functional groups are tolerated, and moderate to good yields of alkenylated products are achieved.
引用
收藏
页码:30134 / 30138
页数:5
相关论文
共 54 条
[1]   Carboxylate-Assisted Ruthenium-Catalyzed Alkyne Annulations by C-H/Het-H Bond Functionalizations [J].
Ackermann, Lutz .
ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (02) :281-295
[2]   Photochemical and Photodynamical Properties of Sulfur-Substituted Nucleic Acid Bases [J].
Ashwood, Brennan ;
Pollum, Marvin ;
Crespo-Hernandez, Carlos E. .
PHOTOCHEMISTRY AND PHOTOBIOLOGY, 2019, 95 (01) :33-58
[3]   Thioketone-Directed Palladium(II)-Catalyzed C-H Arylation of Ferrocenes with Aryl Boronic Acids [J].
Cai, Zhong-Jian ;
Liu, Chen-Xu ;
Gu, Qing ;
You, Shu-Li .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (05) :1296-1299
[4]   Iron-mediated oxidative C-H coupling of arenes and alkenes directed by sulfur: an expedient route to dihydrobenzofurans [J].
Cavanagh, Craig W. ;
Aukland, Miles H. ;
Laurent, Quentin ;
Hennessy, Alan ;
Procter, David J. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (23) :5286-5292
[5]   Bidentate, Monoanionic Auxiliary-Directed Functionalization of Carbon-Hydrogen Bonds [J].
Daugulis, Olafs ;
Roane, James ;
Tran, Ly Dieu .
ACCOUNTS OF CHEMICAL RESEARCH, 2015, 48 (04) :1053-1064
[6]   Two Stereoinduction Events in One C-H Activation Step: A Route towards Terphenyl Ligands with Two Atropisomeric Axes [J].
Dherbassy, Quentin ;
Djukic, Jean-Pierre ;
Wencel-Delord, Joanna ;
Colobert, Francoise .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (17) :4668-4672
[7]  
Emmert M. H., 2016, ARENE CHEM REACTION
[8]   Weak Coordination as a Powerful Means for Developing Broadly Useful C-H Functionalization Reactions [J].
Engle, Keary M. ;
Mei, Tian-Sheng ;
Wasa, Masayuki ;
Yu, Jin-Quan .
ACCOUNTS OF CHEMICAL RESEARCH, 2012, 45 (06) :788-802
[9]   Persulfide synthases that are functionally coupled with translation mediate sulfur respiration in mammalian cells [J].
Fujii, Shigemoto ;
Sawa, Tomohiro ;
Motohashi, Hozumi ;
Akaike, Takaaki .
BRITISH JOURNAL OF PHARMACOLOGY, 2019, 176 (04) :607-615
[10]   Synthesis of Axially Chiral Biaryls through Sulfoxide-Directed Asymmetric Mild C-H Activation and Dynamic Kinetic Resolution [J].
Hazra, Chinmoy Kumar ;
Dherbassy, Quentin ;
Wencel-Delord, Joanna ;
Colobert, Francoise .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (50) :13871-13875