Cu(ClO4)2-Mediated Arene C-H Bond Halogenations of Azacalixaromatics Using Alkali Metal Halides as Halogen Sources

被引：94
作者：
Yao, Bo [2 ]
Wang, Zu-Li [1 ]
Zhang, Hu [2 ]
Wang, De-Xian [2 ]
Zhao, Liang [1 ]
Wang, Mei-Xiang [1 ]
机构：
[1] Tsinghua Univ, Dept Chem, Minist Educ, Key Lab Bioorgan Phosphorus Chem & Chem Biol, Beijing 100084, Peoples R China
[2] Chinese Acad Sci, Inst Chem, CAS Key Lab Mol Recognit & Funct, Beijing Natl Lab Mol Sci, Beijing 100190, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 77卷 / 07期
基金：
中国国家自然科学基金;
关键词：
OXIDATIVE FUNCTIONALIZATION; PI INTERACTIONS; FLUORINATION; ARYL; RECOGNITION; CAVITY; 1,3-ALTERNATE; CONSTRUCTION; COMPLEXATION; RECEPTORS;
D O I：
10.1021/jo300152u
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Regiospecific halogenation of azacalix[1]arene[3]pyridines at the lower rim position of the benzene ring was achieved from their cross-coupling reaction with cost-effective alkali metal halides through the Cu(ClO4)(2)-mediated aerobic aryl C-H activation, which gave structurally well-defined aryl-Cu(III) intermediates, and a subsequent C-X band formation reaction under very mild conditions.
引用
收藏
页码：3336 / 3340
页数：5
相关论文
共 61 条
[1]   On aromatic fluoric compounds, I A new method for its representation [J].
Balz, G ;
Schiemann, G .
BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1927, 60 :1186-1190
[2]  
Bohlmann R., 1991, COMPREHENSIVE ORGANI, V6, P203
[3]   Transition-Metal-Mediated Reactions for Csp2-F Bond Construction: The State of Play [J].
Brown, John M. ;
Gouverneur, Veronique .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (46) :8610-8614
[4]   Nucleophilic Aryl Fluorination and Aryl Halide Exchange Mediated by a CuI/CuIII Catalytic Cycle [J].
Casitas, Alicia ;
Canta, Merce ;
Sola, Miquel ;
Costas, Miguel ;
Ribas, Xavi .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (48) :19386-19392
[5]   Direct observation of CuI/CuIII redox steps relevant to Ullmann-type coupling reactions [J].
Casitas, Alicia ;
King, Amanda E. ;
Parella, Teodor ;
Costas, Miquel ;
Stahl, Shannon S. ;
Ribas, Xavi .
CHEMICAL SCIENCE, 2010, 1 (03) :326-330
[6]   Cu(II)-catalyzed functionalizations of aryl C-H bonds using O2 as an oxidant [J].
Chen, Xiao ;
Hao, Xue-Shi ;
Goodhue, Charles E. ;
Yu, Jin-Quan .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (21) :6790-6791
[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]   Ion pair receptors based on anion-π interaction [J].
Chen, Yin ;
Wang, De-Xian ;
Huang, Zhi-Tang ;
Wang, Mei-Xiang .
CHEMICAL COMMUNICATIONS, 2011, 47 (28) :8112-8114
[9]   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
[10]   A highly selective catalytic method for the oxidative functionalization of C-H bonds [J].
Dick, AR ;
Hull, KL ;
Sanford, MS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (08) :2300-2301
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