PALLADIUM-CATALYZED DIRECT ARYLATION AND ALKENYLATION OF 3-(INDOL-3-YL)PROPIONIC ACIDS THROUGH C-H BOND CLEAVAGE

被引：5
作者：
Takeda, Daisuke [1 ]
Hirano, Koji [1 ]
Satoh, Tetsuya [1 ,2 ]
Miura, Masahiro [1 ]
机构：
[1] Osaka Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan
[2] JST, ACTC, Kawaguchi, Saitama 3320012, Japan
来源：
HETEROCYCLES | 2014年 / 88卷 / 01期
关键词：
C-H Bond Cleavage; Arylation; Alkenylation; Indole; Palladium Catalyst; HETEROAROMATIC-COMPOUNDS; COMBINATORIAL SYNTHESIS; COUPLING REACTIONS; ROOM-TEMPERATURE; ARYL HALIDES; FUNCTIONALIZATION; INDOLES; CARBON; DISCOVERY; ALKYNES;
D O I：
10.3987/COM-13-S(S)13
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The palladium-catalyzed direct arylation of 3-(indol-3-yl)propionic acids with aryl bromides proceeds through C H bond cleavages to give C2-arylated product in good yields. The C2-alkenylation of the substrates can also be performed smoothly under appropriate oxidative conditions.
引用
收藏
页码：275 / 286
页数：12
相关论文
共 79 条
[1]   Carboxylate-Assisted Transition-Metal-Catalyzed C-H Bond Functionalizations: Mechanism and Scope [J].
Ackermann, Lutz .
CHEMICAL REVIEWS, 2011, 111 (03) :1315-1345
[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]   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
[4]   The copper-catalyzed N-arylation of indoles [J].
Antilla, JC ;
Klapars, A ;
Buchwald, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (39) :11684-11688
[5]   C-C, C-O, C-N bond formation on sp2 carbon by Pd(II)-catalyzed reactions involving oxidant agents [J].
Beccalli, Egle M. ;
Broggini, Gianluigi ;
Martinelli, Michela ;
Sottocornola, Silvia .
CHEMICAL REVIEWS, 2007, 107 (11) :5318-5365
[6]   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
[7]   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
[8]   Recent advances in the transition metal-catalyzed twofold oxidative C-H bond activation strategy for C-C and C-N bond formation [J].
Cho, Seung Hwan ;
Kim, Ji Young ;
Kwak, Jaesung ;
Chang, Sukbok .
CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) :5068-5083
[9]   Rhodium Catalyzed Chelation-Assisted C-H Bond Functionalization Reactions [J].
Colby, Denise A. ;
Tsai, Andy S. ;
Bergman, Robert G. ;
Ellman, Jonathan A. .
ACCOUNTS OF CHEMICAL RESEARCH, 2012, 45 (06) :814-825
[10]   Rhodium-Catalyzed C-C Bond Formation via Heteroatom-Directed C-H Bond Activation [J].
Colby, Denise A. ;
Bergman, Robert G. ;
Ellman, Jonathan A. .
CHEMICAL REVIEWS, 2010, 110 (02) :624-655
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