Ruthenium-Catalyzed Heteroatom-Directed Regioselective C-H Arylation of Indoles Using a Removable Tether

被引：84
作者：
Tiwari, Virendra Kumar [1 ]
Kamal, Neha [1 ]
Kapur, Manmohan [1 ]
机构：
[1] Indian Inst Sci Educ & Res Bhopal, Dept Chem, Bhopal 462066, India
来源：
ORGANIC LETTERS | 2015年 / 17卷 / 07期
关键词：
DIRECT C-2 ARYLATION; BOND ARYLATION; ROOM-TEMPERATURE; FREE (NH)-INDOLES; COUPLING REACTION; PALLADIUM; FUNCTIONALIZATION; ACIDS; (HETERO)ARENES; ACTIVATION;
D O I：
10.1021/acs.orglett.5b00535
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new approach to C-2 arylated indoles has been developed by utilizing a ruthenium-catalyzed, heteroatom-directed regioselective C-H arylation. The reaction is highly site-selective and results in very good yields. The highlight of the work is the use of a removable directing group and compatibility of the catalytic system with halogen functional groups in the substrates.
引用
收藏
页码：1766 / 1769
页数：4
相关论文
共 94 条
[1]   Carboxylate-Assisted Ruthenium-Catalyzed Alkyne Annulations by C-H/Het-H Bond Functionalizations [J].
Ackermann, Lutz .
ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (02) :281-295
[2]   Ruthenium-Catalyzed Direct C-H Bond Arylations of Heteroarenes [J].
Ackermann, Lutz ;
Lygin, Alexander V. .
ORGANIC LETTERS, 2011, 13 (13) :3332-3335
[3]   Mechanistic Insight into Direct Arylations with Ruthenium(II) Carboxylate Catalysts [J].
Ackermann, Lutz ;
Vicente, Ruben ;
Potukuchi, Harish K. ;
Pirovano, Valentina .
ORGANIC LETTERS, 2010, 12 (21) :5032-5035
[4]   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
[5]   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
[6]   Cyclometalation Using d-Block Transition Metals: Fundamental Aspects and Recent Trends [J].
Albrecht, Martin .
CHEMICAL REVIEWS, 2010, 110 (02) :576-623
[7]   Structure-activity relationships of 2-aryl-1H-indole inhibitors of the NorA efflux pump in Staphylococcus aureus [J].
Ambrus, Joseph I. ;
Kelso, Michael J. ;
Bremner, John B. ;
Ball, Anthony R. ;
Casadei, Gabriele ;
Lewis, Kim .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (15) :4294-4297
[8]   Copper-mediated C-H bond arylation of arenes with arylboronic acids [J].
Ban, Ikuya ;
Sudo, Tomoko ;
Taniguchi, Tadashi ;
Itami, Kenichiro .
ORGANIC LETTERS, 2008, 10 (16) :3607-3609
[9]   Palladium- and copper-mediated direct C-2 arylation of azoles - Including free (NH)-imidazole, -benzimidazole and -indole - Under base-free and ligandless conditions [J].
Bellina, F ;
Cauteruccio, S ;
Rossi, R .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (06) :1379-1382
[10]  
Bergman RG, 2007, NATURE, V446, P391, DOI 10.1038/446391a
12345678910