Rhodium-Catalyzed ortho-Selective C-F Activation and Hydrodefluorination of Heterocycle-Substituted Polyfluoroarenes: Dominated by Phosphine Ligands

被引:8
作者
Chen, Jianping [1 ]
Huang, Dongyang [1 ]
Ding, Yuqiang [1 ]
机构
[1] Jiangnan Univ, Minist Educ, Sch Chem & Mat Engn, Key Lab Food Colloids & Biotechnol, Wuxi 214122, Jiangsu, Peoples R China
基金
中国国家自然科学基金;
关键词
C-F bond; Hydrodefluorination; Phosphine ligand; Rhodium; Selective; CARBON-FLUORINE BONDS; TRANSITION-METAL-COMPLEXES; DIRECT ARYLATIONS; ROOM-TEMPERATURE; BUILDING-BLOCKS; BORYL COMPLEXES; FACILE ACCESS; FLUOROARENES; REACTIVITY; FUNCTIONALIZATION;
D O I
10.1002/slct.201601839
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
In this paper, the ortho-selective mono-hydrodefluorination and/or di-hydrodefluorination of heterocycle substituted poly-fluoroarenes were catalyzed by rhodium complexes along with phosphine ligands and ethanol as hydride source. Diverse partially fluorinated aromatics had been synthesized by this method. The study of the mechanism demonstrated that ethanol was the sole hydride source in the cycle of hydro-defluorination. Furthermore, the phosphine ligand controlled chemoselectivity had been discussed by monitoring experiment.
引用
收藏
页码:1219 / 1224
页数:6
相关论文
共 92 条
[1]  
Ahrens M., 2013, ANGEW CHEM, V125, P5436
[2]   Catalytic Hydrodefluorination of Fluoromethanes at Room Temperature by Silylium-ion-like Surface Species [J].
Ahrens, Mike ;
Scholz, Gudrun ;
Braun, Thomas ;
Kemnitz, Erhard .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (20) :5328-5332
[3]   Synthesis of a rhodium(I) germyl complex: a useful tool for C-H and C-F bond activation reactions [J].
Ahrens, Theresia ;
Ahrens, Mike ;
Braun, Thomas ;
Braun, Beatrice ;
Herrmann, Roy .
DALTON TRANSACTIONS, 2016, 45 (11) :4716-4728
[4]   Functionalization of Fluorinated Molecules by Transition-Metal-Mediated C-F Bond Activation To Access Fluorinated Building Blocks [J].
Ahrens, Theresia ;
Kohlmann, Johannes ;
Ahrens, Mike ;
Braun, Thomas .
CHEMICAL REVIEWS, 2015, 115 (02) :931-972
[5]   HOMOGENEOUS METAL-CATALYZED HYDROGENOLYSIS OF C-F BONDS [J].
AIZENBERG, M ;
MILSTEIN, D .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (33) :8674-8675
[6]   CATALYTIC ACTIVATION OF CARBON-FLUORINE BONDS BY A SOLUBLE TRANSITION-METAL COMPLEX [J].
AIZENBERG, M ;
MILSTEIN, D .
SCIENCE, 1994, 265 (5170) :359-361
[7]   C-F Bond Activation in Organic Synthesis [J].
Amii, Hideki ;
Uneyama, Kenji .
CHEMICAL REVIEWS, 2009, 109 (05) :2119-2183
[8]  
[Anonymous], 2012, ANGEW CHEM
[9]  
[Anonymous], ANGEW CHEM
[10]  
[Anonymous], 2012, Phosphorus(III) Ligands in Homogeneous Catalysis: Design and Synthesis