Amide-Ligand-Controlled Highly para-Selective Arylation of Monosubstituted Simple Arenes with Arylboronic Acids

被引:64
作者
Luan, Yu-Xin [1 ,2 ]
Zhang, Tao [1 ,2 ]
Yao, Wei-Wei [1 ,2 ]
Lu, Ke [1 ,2 ]
Kong, Lu-Yao [1 ,2 ]
Lin, Yu-Tong [1 ,2 ]
Ye, Mengchun [1 ,2 ,3 ]
机构
[1] Nankai Univ, State Key Lab, Tianjin 300071, Peoples R China
[2] Nankai Univ, Inst Elementoorgan Chem, Tianjin 300071, Peoples R China
[3] Nankai Univ, Collaborat Innovat Ctr Chem Sci & Engn Tianjin, Tianjin 300071, Peoples R China
基金
中国国家自然科学基金;
关键词
CATALYZED DIRECT ARYLATION; C-H ACTIVATION; ELECTRON-DEFICIENT POLYFLUOROARENES; CROSS-COUPLING REACTIONS; ARYL BOND FORMATION; UNACTIVATED ARENES; SODIUM PERSULFATE; ROOM-TEMPERATURE; PALLADIUM; FUNCTIONALIZATION;
D O I
10.1021/jacs.6b12907
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Pd-catalyzed highly para-selective arylations of monosubstituted simple arenes with arylboronic acids to widely existed biaryls have been developed. Inspired by requisite amide-directing groups in reported selective oxidative couplings, amide ligands, especially DMF, are designed and found to be critical for the selectivity control in current arylations.
引用
收藏
页码:1786 / 1789
页数:4
相关论文
共 73 条
[1]   Transition-Metal-Catalyzed Direct Arylation of (Hetero)Arenes by C-H Bond Cleavage [J].
Ackermann, Lutz ;
Vicente, Ruben ;
Kapdi, Anant R. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (52) :9792-9826
[2]   Aryl-aryl bond formation by transition-metal-catalyzed direct arylation [J].
Alberico, Dino ;
Scott, Mark E. ;
Lautens, Mark .
CHEMICAL REVIEWS, 2007, 107 (01) :174-238
[3]   Intermolecular oxidative cross-coupling of arenes [J].
Ashenhurst, James A. .
CHEMICAL SOCIETY REVIEWS, 2010, 39 (02) :540-548
[4]   Gold-Catalyzed Oxidative Coupling of Arylsilanes and Arenes: Origin of Selectivity and Improved Precatalyst [J].
Ball, Liam T. ;
Lloyd-Jones, Guy C. ;
Russell, Christopher A. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (01) :254-264
[5]   Gold-Catalyzed Direct Arylation [J].
Ball, Liam T. ;
Lloyd-Jones, Guy C. ;
Russell, Christopher A. .
SCIENCE, 2012, 337 (6102) :1644-1648
[6]   Twofold C-H functionalization:: Palladium-catalyzed ortho arylation of anilides [J].
Brasche, Gordon ;
Garcia-Fortanet, Jorge ;
Buchwald, Stephen L. .
ORGANIC LETTERS, 2008, 10 (11) :2207-2210
[7]   Atroposelective Total Synthesis of Axially Chiral Biaryl Natural Products [J].
Bringmann, Gerhard ;
Gulder, Tanja ;
Gulder, Tobias A. M. ;
Breuning, Matthias .
CHEMICAL REVIEWS, 2011, 111 (02) :563-639
[8]   Au-Catalyzed Cross-Coupling of Arenes via Double C-H Activation [J].
Cambeiro, Xacobe C. ;
Ahlsten, Nanna ;
Larrosa, Igor .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (50) :15636-15639
[9]   Redox-Controlled Selectivity of C-H Activation in the Oxidative Cross-Coupling of Arenes [J].
Cambeiro, Xacobe C. ;
Boorman, Tanya C. ;
Lu, Pengfei ;
Larrosa, Igor .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (06) :1781-1784
[10]  
Campeau LC, 2007, ALDRICHIM ACTA, V40, P35