Metal-free electrophilic phosphination of electron-rich arenes, arenols and aromatic thiols with diarylphosphine oxides

被引：37
作者：
Yuan, Tao [1 ]
Huang, Shenlin [2 ]
Cai, Chun [1 ]
Lu, Guo-ping [1 ]
机构：
[1] Nanjing Univ Sci & Technol, Chem Engn Coll, Xiaolingwei 200, Nanjing 210094, Jiangsu, Peoples R China
[2] Nanjing Forestry Univ, Jiangsu Key Lab Biomass Based Green Fuels & Chem, Coll Chem Engn, Nanjing 210037, Jiangsu, Peoples R China
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2018年 / 16卷 / 01期
关键词：
CROSS-COUPLING REACTIONS; BOND FORMATION; REGIOSELECTIVE SYNTHESIS; IONIC LIQUIDS; LIGANDS; DERIVATIVES; WATER; MILD; KETOPHOSPHONATES; PHOSPHORYLATION;
D O I：
10.1039/c7ob02620j
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new protocol for achieving the phosphination of arenes, arenols and thiols has been disclosed. This chemistry, in which diaryl(((trifluoromethyl) sulfonyl)oxy)phosphines as a kind of electrophilic phosphination reagents are in situ generated from diarylphosphine oxides, provides an efficient and mild approach for the synthesis of aromatic organophosphorus compounds.
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收藏
页码：30 / 33
页数：4
相关论文
共 51 条
[1]  
Ang J., 2015, J AM CHEM SOC, V137, P1782
[2]   Rhodium-catalyzed thiophosphinylation and phosphinylation reactions of disulfides and diselenides [J].
Arisawa, M ;
Ono, T ;
Yamaguchi, M .
TETRAHEDRON LETTERS, 2005, 46 (34) :5669-5671
[3]   THE PREPARATION AND PROPERTIES OF TERTIARY AND SECONDARY PHOSPHINE OXIDES [J].
BERLIN, KD ;
BUTLER, GB .
CHEMICAL REVIEWS, 1960, 60 (03) :243-260
[4]   Generation of phosphorus-centered radicals via homolytic substitution at sulfur [J].
Carta, Paola ;
Puljic, Nicolas ;
Robert, Carine ;
Dhimane, Anne-Lise ;
Fensterbank, Louis ;
Lacote, Emmanuel ;
Malacria, Max .
ORGANIC LETTERS, 2007, 9 (06) :1061-1063
[5]   Metal-free O-H/C-H difunctionalization of phenols by o-hydroxyarylsulfonium salts in water [J].
Chen, Dengfeng ;
Feng, Qingyuan ;
Yang, Yunqin ;
Cai, Xu-Min ;
Wang, Fei ;
Huang, Shenlin .
CHEMICAL SCIENCE, 2017, 8 (02) :1601-1606
[6]   Peroxides as "Switches" of Dialkyl H-Phosphonate: Two Mild and Metal-Free Methods for Preparation of 2-Acylbenzothiazoles and Dialkyl Benzothiazol-2-ylphosphonates [J].
Chen, Xiao-Lan ;
Li, Xu ;
Qu, Ling-Bo ;
Tang, Yu-Chun ;
Mai, Wen-Peng ;
Wei, Dong-Hui ;
Bi, Wen-Zhu ;
Duan, Li-Kun ;
Sun, Kai ;
Chen, Jian-Yu ;
Ke, Dian-Dian ;
Zhao, Yu-Fen .
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (17) :8407-8416
[7]   Structure-Guided Design, Synthesis, and Evaluation of Guanine-Derived Inhibitors of the eIF4E mRNA-Cap Interaction [J].
Chen, Xiaoqi ;
Kopecky, David J. ;
Mihalic, Jeff ;
Jeffries, Shawn ;
Min, Xiaoshan ;
Heath, Julie ;
Deignan, Jeff ;
Lai, SuJen ;
Fu, Zice ;
Guimaraes, Cristiano ;
Shen, Shanling ;
Li, Shyun ;
Johnstone, Sheree ;
Thibault, Stephen ;
Xu, Haoda ;
Cardozo, Mario ;
Shen, Wang ;
Walker, Nigel ;
Kayser, Frank ;
Wang, Zhulun .
JOURNAL OF MEDICINAL CHEMISTRY, 2012, 55 (08) :3837-3851
[8]   Discovery of a Series of Phosphonic Acid-Containing Thiazoles and Orally Bioavailable Diamide Prodrugs That Lower Glucose in Diabetic Animals Through Inhibition of Fructose-1,6-Bisphosphatase [J].
Dang, Qun ;
Liu, Yan ;
Cashion, Daniel K. ;
Kasibhatla, Srinivas Rao ;
Jiang, Tao ;
Taplin, Frank ;
Jacintho, Jason D. ;
Li, Haiqing ;
Sun, Zhili ;
Fan, Yi ;
DaRe, Jay ;
Tian, Feng ;
Li, Wenyu ;
Gibson, Tony ;
Lemus, Robert ;
van Poelje, Paul D. ;
Potter, Scott C. ;
Erion, Mark D. .
JOURNAL OF MEDICINAL CHEMISTRY, 2011, 54 (01) :153-165
[9]   Synthesis, structure-activity relationships, and biological evaluation of fatty alcohol phosphates as lysophosphatidic acid receptor ligands, activators of PPARγ, and inhibitors of autotaxin [J].
Durgam, GG ;
Virag, T ;
Walker, MD ;
Tsukahara, R ;
Yasuda, S ;
Liliom, K ;
van Meeteren, LA ;
Moolenaar, WH ;
Wilke, N ;
Siess, W ;
Tigyi, G ;
Miller, DD .
JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (15) :4919-4930
[10]   Phosphine-Phosphinite and Phosphine-Phosphite Ligands: Preparation and Applications in Asymmetric Catalysis [J].
Fernandez-Perez, Hector ;
Etayo, Pablo ;
Panossian, Armen ;
Vidal-Ferran, Anton .
CHEMICAL REVIEWS, 2011, 111 (03) :2119-2176
123456