Palladium-Catalyzed β-Selective Direct Arylation of Porphyrins

被引：37
作者：
Kawamata, Yu [1 ]
Tokuji, Sumito [1 ]
Yorimitsu, Hideki [1 ]
Osuka, Atsuhiro [1 ]
机构：
[1] Kyoto Univ, Grad Sch Sci, Dept Chem, Sakyo Ku, Kyoto 6068502, Japan
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2011年 / 50卷 / 38期
关键词：
arylation; C-H activation; palladium; porphyrinoids; H BOND ARYLATION; MULTIPLE ARYLATION; METAL; FUNCTIONALIZATION; MECHANISM; REAGENTS;
D O I：
10.1002/anie.201102318
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Four birds with one stone: A palladium catalyst/potassium carbonate/pivalic acid system enables direct arylation of porphyrins by aryl bromides (see scheme; Ar=3,5-tBu2C6H3). The C-H arylation shows excellent β selectivity and does not require porphyrin prefunctionalization, hence representing an extremely efficient method for rapidly providing a series of new β-arylated porphyrins. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
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收藏
页码：8867 / 8870
页数：4
相关论文
共 71 条
[1]  
Ackermann L., 2009, ANGEW CHEM, V121, P9976, DOI DOI 10.1002/ANGE.200902996
[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]  
[Anonymous], 2008, ANGEW CHEM
[5]  
[Anonymous], 2010, C H ACTIVATION
[6]   Discrete Cyclic Porphyrin Arrays as Artificial Light-Harvesting Antenna [J].
Aratani, Naoki ;
Kim, Dongho ;
Osuka, Atsuhiro .
ACCOUNTS OF CHEMICAL RESEARCH, 2009, 42 (12) :1922-1934
[7]   π-Conjugation Enlargement Toward the Creation of Multi-Porphyrinic Systems with Large Two-Photon Absorption Properties [J].
Aratani, Naoki ;
Kim, Dongho ;
Osuka, Atsuhiro .
CHEMISTRY-AN ASIAN JOURNAL, 2009, 4 (08) :1172-1182
[8]   Porphyrins with metal, metalloid or phosphorus atoms directly bonded to the carbon periphery [J].
Atefi, Farzad ;
Arnold, Dennis P. .
JOURNAL OF PORPHYRINS AND PHTHALOCYANINES, 2008, 12 (07) :801-831
[9]   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
[10]  
Bard A., 1994, INTEGRATED CHEM SYST
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