Organocatalysis in Cross-Coupling: DMEDA-Catalyzed Direct C-H Arylation of Unactivated Benzene

被引:520
作者
Liu, Wei [3 ]
Cao, Hao [3 ]
Zhang, Hua [3 ]
Zhang, Heng [3 ]
Chung, Kin Ho [1 ,2 ]
He, Chuan [3 ]
Wang, Haibo [3 ]
Kwong, Fuk Yee [1 ,2 ]
Lei, Aiwen [3 ,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] Wuhan Univ, Coll Chem & Mol Sci, Wuhan 430072, Hubei, Peoples R China
[4] Chinese Acad Sci, Shanghai Inst Organ Chem, Lab Organometall Chem, Shanghai 200032, Peoples R China
关键词
BOND ARYLATION; ARYL BROMIDES; N-OXIDES; HETEROCYCLES; INDOLES; ALKENYLATION; HETEROARENES; ACTIVATION; ARENES; SCOPE;
D O I
10.1021/ja103050x
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A striking breakthrough to the frame of traditional cross-couplings/C-H functionalizations using an organocatalyst remains unprecedented. We uncovered a conceptually different approach toward the biaryl syntheses by using DMEDA as the catalyst to promote the direct C-H arylation of unactivated benzene in the presence of potassium tert-butoxide. The arylation of unactivated benzene with aryl iodides, or aryl bromides and even chlorides under the assistance of an iodo-group, could simply take place at 80 degrees C. The new methodology presumably involves an aryl radical anion as an intermediate. This finding offers an option toward establishing a new horizon for direct C-H/cross-coupling reactions.
引用
收藏
页码:16737 / 16740
页数:4
相关论文
共 40 条
[1]   Palladium-Catalyzed Direct Arylations of Heteroarenes with Tosylates and Mesylates [J].
Ackermann, Lutz ;
Althammer, Andreas ;
Fenner, Sabine .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (01) :201-204
[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]   Direct Transition-Metal-Free Intramolecular Arylation of Phenols [J].
Bajracharya, Gan B. ;
Daugulis, Olafs .
ORGANIC LETTERS, 2008, 10 (20) :4625-4628
[4]   Rh(I)-Catalyzed Direct Arylation of Pyridines and Quinolines [J].
Berman, Ashley M. ;
Lewis, Jared C. ;
Bergman, Robert G. ;
Ellman, Jonathan A. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (45) :14926-+
[5]   Organocatalysis-after the gold rush [J].
Bertelsen, Soren ;
Jorgensen, Karl Anker .
CHEMICAL SOCIETY REVIEWS, 2009, 38 (08) :2178-2189
[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]   Palladium-Catalyzed Direct Arylation of Azine and Azole N-Oxides: Reaction Development, Scope and Applications in Synthesis [J].
Campeau, Louis-Charles ;
Stuart, David R. ;
Leclerc, Jean-Philippe ;
Bertrand-Laperle, Megan ;
Villemure, Elisia ;
Sun, Ho-Yan ;
Lasserre, Sandrine ;
Guimond, Nicolas ;
Lecavallier, Melanie ;
Fagnou, Keith .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (09) :3291-3306
[8]   Nickel-Catalyzed Biaryl Coupling of Heteroarenes and Aryl Halides/Triflates [J].
Canivet, Jerome ;
Yamaguchi, Junichiro ;
Ban, Ikuya ;
Itami, Kenichiro .
ORGANIC LETTERS, 2009, 11 (08) :1733-1736
[9]   Two methods for direct ortho-arylation of benzoic acids [J].
Chiong, Hendrich A. ;
Pham, Quynh-Nhu ;
Daugulis, Olafs .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (32) :9879-9884
[10]   Palladium-catalyzed C-H functionalization of pyridine N-oxides:: Highly selective alkenylation and direct arylation with unactivated arenes [J].
Cho, Seung Hwan ;
Hwang, Seung Jun ;
Chang, Sukbok .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (29) :9254-+