Fast and Selective Dehydrogenative C-H/C-H Arylation Using Niechanochemistry

被引:105
作者
Lou, Shao-Jie [1 ]
Mao, Yang-Jie [1 ]
Xu, Dan-Qian [1 ]
He, Jiang-Qi [1 ]
Chen, Qi [1 ]
Xu, Zhen-Yuan [1 ]
机构
[1] Zhejiang Univ Technol, State Key Lab Breeding Base Green Chem Synth Tech, Catalyt Hydrogenat Res Ctr, Hangzhou 310014, Zhejiang, Peoples R China
基金
中国博士后科学基金;
关键词
mechanochemistry; C-H bond activation; selective arylation; biaryls; ball milling; CATALYZED ORTHO-ARYLATION; ARYL BOND FORMATION; COUPLING REACTIONS; BENZAMIDES; ARENES; FUNCTIONALIZATION; MECHANOCHEMISTRY; ACTIVATION; AMIDATION; AZIDES;
D O I
10.1021/acscatal.6b00861
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
A fast and site-selective biaryl synthesis via dehydrogenative C-H/C-H arylation in a ball mill was developed. In this paper, both electron-deficient oximes and electron-rich anilides quickly and under mild conditions provided arylation with various arenes to give the biaryl products in high-level selectivity. Given the solventless mechanochemical conditions, the transformation obviated the use of large amounts of arene coupling partners as solvents and allowed utilization of more-complicated and more-expensive arenes as coupling partners, which may dramatically enhance the application prospect of the C-H/C-H arylation strategy.
引用
收藏
页码:3890 / 3894
页数:5
相关论文
共 56 条
[41]   Pd-Catalyzed Multiple C-H Functionalization to Construct Biologically Active Compounds from Aryl Aldoxime Ethers with Arenes [J].
Thirunavukkarasu, Vedhagiri S. ;
Cheng, Chien-Hong .
CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (52) :14723-14726
[42]   Intermolecular amidation of unactivated sp2 and sp3 C-H bonds via palladium-catalyzed cascade C-H activation/nitrene insertion [J].
Thu, Hung-Yat ;
Yu, Wing-Yiu ;
Che, Chi-Ming .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (28) :9048-9049
[43]   Carbon-hydrogen (C-H) bond activation at PdIV: a Frontier in C-H functionalization catalysis [J].
Topczewski, Joseph J. ;
Sanford, Melanie S. .
CHEMICAL SCIENCE, 2015, 6 (01) :70-76
[44]   Platinum-Catalyzed C-H Arylation of Simple Arenes [J].
Wagner, Anna M. ;
Hickman, Amanda J. ;
Sanford, Melanie S. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (42) :15710-15713
[45]   Mechanochemical organic synthesis [J].
Wang, Guan-Wu .
CHEMICAL SOCIETY REVIEWS, 2013, 42 (18) :7668-7700
[46]   Pd(II)-Catalyzed para-Selective C-H Arylation of Monosubstituted Arenes [J].
Wang, Xisheng ;
Leow, Dasheng ;
Yu, Jin-Quan .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (35) :13864-13867
[47]   Pd(OAc)2-Catalyzed Oxidative C-H/C-H Cross-Coupling of Electron-Deficient Polyfluoroarenes with Simple Arenes [J].
Wei, Ye ;
Su, Weiping .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (46) :16377-16379
[48]   [RhIIICp*]-Catalyzed Dehydrogenative Aryl?Aryl Bond Formation [J].
Wencel-Delord, Joanna ;
Nimphius, Corinna ;
Patureau, Frederic W. ;
Glorius, Frank .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (09) :2247-2251
[49]   Towards mild metal-catalyzed C-H bond activation [J].
Wencel-Delord, Joanna ;
Droege, Thomas ;
Liu, Fan ;
Glorius, Frank .
CHEMICAL SOCIETY REVIEWS, 2011, 40 (09) :4740-4761
[50]   Ligand-Controlled Para-Selective C-H Arylation of Monosubstituted Arenes [J].
Xu, Hui ;
Shang, Ming ;
Dai, Hui-Xiong ;
Yu, Jin-Quan .
ORGANIC LETTERS, 2015, 17 (15) :3830-3833