Direct C-H Functionalization of Heteroarenes via Redox-Neutral Radical Process: A Facile Route to C-C Bonds Formation

被引:34
作者
Gao, Pin
Gu, Yu-Rui
Duan, Xin-Hua [1 ]
机构
[1] Xi An Jiao Tong Univ, Dept Chem, Sch Sci, Xian 710049, Peoples R China
来源
SYNTHESIS-STUTTGART | 2017年 / 49卷 / 15期
关键词
C-H functionalization; heteroarenes; redox-neutral; C-C bonds formation; radical reactions; LIGHT PHOTOREDOX CATALYSIS; ELECTRON-RICH HETEROCYCLES; CROSS-COUPLING REACTIONS; TERTIARY ALKYL-HALIDES; ARYL DIAZONIUM SALTS; DIARYLIODONIUM SALTS; METAL-FREE; ROOM-TEMPERATURE; DIRECT ARYLATION; N-HETEROARENES;
D O I
10.1055/s-0036-1588493
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Aromatic heterocycles are an important class of compounds found in a wide range of natural products, pharmaceutically active molecules and organic materials. Recently, the direct radical functionalization of heteroaromatic C-H bonds has become an efficient and attractive method to access substituted heteroarenes. Especially, redoxneutral radical reactions have attracted much attention of chemists due to their potential advantages such as mild conditions, free of external oxidants, and good functional group tolerance. So far, a series of redoxneutral radical reactions have been developed. In this review, we mainly focus on the recent advance in direct redox-neutral radical C-H functionalization of heteroarenes. Herein, the direct C-H arylation, C-H alkylation, and C-H fluoroalkylation of heteroarenes are represented respectively, providing practical routes to C-C bond formation.
引用
收藏
页码:3407 / 3421
页数:15
相关论文
共 108 条
[1]   User-Friendly [(Diglyme)NiBr2]-Catalyzed Direct Alkylations of Heteroarenes with Unactivated Alkyl Halides through C-H Bond Cleavages [J].
Ackermann, Lutz ;
Punji, Benudhar ;
Song, Weifeng .
ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (18) :3325-3329
[2]   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
[3]   N-Acyloxyphthalimides as Nitrogen Radical Precursors in the Visible Light Photocatalyzed Room Temperature C-H Amination of Arenes and Heteroarenes [J].
Allen, Laura J. ;
Cabrera, Pablo J. ;
Lee, Melissa ;
Sanford, Melanie S. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (15) :5607-5610
[4]   Carbon Trifluoromethylation Reactions of Hydrocarbon Derivatives and Heteroarenes [J].
Alonso, Concepcion ;
Martinez de Marigorta, Eduardo ;
Rubiales, Gloria ;
Palacios, Francisco .
CHEMICAL REVIEWS, 2015, 115 (04) :1847-1935
[5]   Polyaniline-Induced CH Arylation of Arenes with Arenediazonium Salts [J].
Amaya, Toru ;
Hata, Dai ;
Moriuchi, Toshiyuki ;
Hirao, Toshikazu .
CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (46) :16427-16433
[6]  
[Anonymous], 2012, SYNTHESIS
[7]   Photocatalytic Generation of 2-Azolyl Radicals: Intermediates for the Azolylation of Arenes and Heteroarenes via C-H Functionalization [J].
Arora, Amandeep ;
Weaver, Jimmie D. .
ORGANIC LETTERS, 2016, 18 (16) :3996-3999
[8]   Perfluoroalkylation reactions of (hetero)arenes [J].
Barata-Vallejo, Sebastian ;
Bonesi, Sergio M. ;
Postigo, Al .
RSC ADVANCES, 2015, 5 (77) :62498-62518
[9]   New approaches for decarboxylative biaryl coupling [J].
Baudoin, Olivier .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (09) :1373-1375
[10]   Transition Metal-Mediated Direct C-H Arylation of Heteroarenes Involving Aryl Radicals [J].
Bonin, Helene ;
Sauthier, Mathieu ;
Felpin, Francois-Xavier .
ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (04) :645-671