An Efficient Oxidative Cross-Coupling Reaction between C-H and N-H Bonds; A Transition-Metal-Free Protocol at Room Temperature

被引：21

作者：

Wu, Yinuo ^{[1
,2
]}

Kwong, Fuk Yee ^{[1
,2
]}

Li, Pengfei ^{[1
,2
,3
]}

Chan, Albert S. C. ^{[4
]}

机构：

[1] Hong Kong Polytech Univ, State Key Lab Chirosci, Hong Kong, Hong Kong, Peoples R China

[2] Hong Kong Polytech Univ, Dept Appl Biol & Chem Technol, Hong Kong, Hong Kong, Peoples R China

[3] South Univ Sci & Technol China, Dept Chem, Shenzhen, Guangdong, Peoples R China

[4] Hong Kong Baptist Univ, Inst Creat, Hong Kong, Hong Kong, Peoples R China

来源：

SYNLETT | 2013年 / 24卷 / 15期

关键词：

metal-free; cross-coupling; oxidative coupling; amination; C-H activation; POTASSIUM TERT-BUTOXIDE; UNACTIVATED ARENES; DIRECT ARYLATION; ARYL HALIDES; AMINATION; ACTIVATION; BENZENE; HETEROCYCLES; CATALYSTS; REAGENTS;

D O I：

10.1055/s-0033-1339447

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A transition-metal-free oxidative coupling of allylic C-H and heterocyclic/aromatic N-H bonds was performed under mild conditions. Promoted by 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ), up to 99% yield could be achieved.

引用

页码：2009 / 2013

页数：5

共 55 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] Organocatalytic, Oxidative, Intramolecular C-H Bond Amination and Metal-free Cross-Amination of Unactivated Arenes at Ambient Temperature [J].

Antonchick, Andrey P. ;

Samanta, Rajarshi ;

Kulikov, Katharina ;

Lategahn, Jonas .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (37) :8605-8608

[3] Direct Azole Amination: C-H Functionalization as a New Approach to Biologically Important Heterocycles [J].

Armstrong, Alan ;

Collins, James C. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (13) :2282-2285

[4]

Beller M., 2004, Transition Metals for Organic Synthesis, V1, P2

[5] Recent advances in the synthesis of (hetero)aryl-substituted heteroarenes via transition metal-catalysed direct (hetero)arylation of heteroarene C-H bonds with aryl halides or pseudohalides, diaryliodonium salts, and potassium aryltrifluoroborates [J].

Bellina, Fabio ;

Rossi, Renzo .

TETRAHEDRON, 2009, 65 (50) :10269-10310

[6] Transition-Metal-Free Synthesis of Oxindoles by Potassium tert-Butoxide-Promoted intramolecular α-Arylation [J].

Beyer, Astrid ;

Buendia, Julien ;

Bolm, Carsten .

ORGANIC LETTERS, 2012, 14 (15) :3948-3951

[7] 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

[8] 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

[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] Palladium(II)-Catalyzed C-H Activation/C-C Cross-Coupling Reactions: Versatility and Practicality [J].

Chen, Xiao ;

Engle, Keary M. ;

Wang, Dong-Hui ;

Yu, Jin-Quan .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (28) :5094-5115

← 1 2 3 4 5 6 →