Phenyl Hydrazine as Initiator for Direct Arene C-H Arylation via Base Promoted Homolytic Aromatic Substitution

被引:110
作者
Dewanji, Abhishek
Murarka, Sandip
Curran, Dennis P.
Studer, Armido
机构
[1] Univ Munster, NRW Grad Sch Chem, Inst Organ Chem, D-48149 Munster, Germany
[2] Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA
关键词
ARYL BOND FORMATION; UNACTIVATED ARENES; BUTOXIDE; HALIDES; ACTIVATION; BENZENE;
D O I
10.1021/ol402995e
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A simple and efficient direct radical arylation of unactivated arenes is described which uses cheap and commercially available phenyl hydrazine as an initiator. The reaction occurs through a base promoted homolytic aromatic substitution (BHAS) mechanism involving aryl radicals and aryl radical anions as intermediates and offers a practical approach for preparation of an array of substituted biaryls.
引用
收藏
页码:6102 / 6105
页数:4
相关论文
共 33 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]  
Arockiam PB, 2012, CHEM REV, V112, P5879, DOI [10.1021/cr300153J, 10.1021/cr300153j]
[4]   KOtBu Mediated Synthesis of Phenanthridinones and Dibenzoazepinones [J].
Bhakuni, Bhagat Singh ;
Kumar, Amit ;
Balkrishna, Shah Jaimin ;
Sheikh, Javeed Ahmed ;
Konar, Sanjit ;
Kumar, Sangit .
ORGANIC LETTERS, 2012, 14 (11) :2838-2841
[5]   Room-Temperature Photoinduced Direct C-H-Arylation via Base-Promoted Homolytic Aromatic Substitution [J].
Buden, Maria E. ;
Guastavino, Javier F. ;
Rossi, Roberto A. .
ORGANIC LETTERS, 2013, 15 (06) :1174-1177
[6]   NUCLEOPHILIC REPLACEMENT OF 2 HALOGENS IN DIHALOBENZENES WITHOUT INTERMEDIACY OF MONOSUBSTITUTION PRODUCTS [J].
BUNNETT, JF ;
CREARY, X .
JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (24) :3611-3612
[7]  
Campeau LC, 2007, ALDRICHIM ACTA, V40, P35
[8]   Base- and metal-free C-H direct arylations of naphthalene and other unbiased arenes with diaryliodonium salts [J].
Castro, Susana ;
Fernandez, Juan J. ;
Vicente, Ruben ;
Fananas, Francisco J. ;
Rodriguez, Felix .
CHEMICAL COMMUNICATIONS, 2012, 48 (72) :9089-9091
[9]   Metal-free arylation of benzene and pyridine promoted by amino-linked nitrogen heterocyclic carbenes [J].
Chen, Wen-Ching ;
Hsu, Yu-Chen ;
Shih, Wei-Chun ;
Lee, Ching-Yu ;
Chuang, Wen-Han ;
Tsai, Yi-Fang ;
Chen, Peter Ping-Yu ;
Ong, Tiow-Gan .
CHEMICAL COMMUNICATIONS, 2012, 48 (53) :6702-6704
[10]   Visible-Light Photoredox in Homolytic Aromatic Substitution: Direct Arylation of Arenes with Aryl Halides [J].
Cheng, Yannan ;
Gu, Xiangyong ;
Li, Pixu .
ORGANIC LETTERS, 2013, 15 (11) :2664-2667