Palladium(II)-Catalyzed Regioselective Arylation of Naphthylamides with Aryl Iodides Utilizing a Quinolinamide Bidentate System

被引：79
作者：
Huang, Lehao [1 ]
Li, Qian [1 ,2 ]
Wang, Chen [1 ]
Qi, Chenze [1 ]
机构：
[1] Shaoxing Univ, Inst Appl Chem, Zhejiang Key Lab Alternat Technol Fine Chem Proc, Shaoxing 312000, Zhejiang, Peoples R China
[2] Ningbo Univ, Coll Mat Sci & Chem Engn, Ningbo 310014, Zhejiang, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 78卷 / 07期
关键词：
CATALYZED DIRECT ARYLATION; C-H ARYLATION; UNACTIVATED C(SP(3))-H; BOND-FORMATION; SIMPLE ARENES; AROMATIC AMIDES; ACTIVATION; RUTHENIUM; FUNCTIONALIZATION; (HETERO)ARENES;
D O I：
10.1021/jo400017v
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A palladium(II)-catalyzed quinolinamide-directed 8-arylation of 1-naphthylamides with aryl iodides is reported. The bidentate directing group (quinolinamide) proved to be crucial for a highly regioselective transformation. In addition, the amide directing group can be easily hydrolyzed under basic conditions to offer a range of 8-aryl-1-naphthylamine derivatives. The theoretical calculations suggest that the C-H arylation reaction proceeds through a sequential C-H activation/oxidative addition pathway.
引用
收藏
页码：3030 / 3038
页数：9
相关论文
共 83 条
[61]  
Vyskocil S, 2002, CHEM-EUR J, V8, P4633, DOI 10.1002/1521-3765(20021018)8:20<4633::AID-CHEM4633>3.0.CO
[62]  
2-N
[63]   Pd(0)/PR3-Catalyzed Intermolecular Arylation of Sp3 C-H Bonds [J].
Wasa, Masayuki ;
Engle, Keary M. ;
Yu, Jin-Quan .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (29) :9886-+
[64]   Rhodium(III) and Hexabromobenzene-A Catalyst System for the Cross-Dehydrogenative Coupling of Simple Arenes and Heterocycles with Arenes Bearing Directing Groups [J].
Wencel-Delord, Joanna ;
Nimphius, Corinna ;
Wang, Honggen ;
Glorius, Frank .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (52) :13001-13005
[65]  
Wigglesworth A., 2012, [No title captured], Patent No. [DE102012201973A1, 102012201973]
[66]   Palladium catalyzed synthesis of highly substituted naphthalenes via direct ring construction from amides with alkynes [J].
Wu, Junliang ;
Cui, Xiuling ;
Mi, Xia ;
Li, Ying ;
Wu, Yangjie .
CHEMICAL COMMUNICATIONS, 2010, 46 (36) :6771-6773
[67]   Carbon-carbon bond formation through double Sp2 C-H activations:: Synthesis of ferrocenyl oxazoline derivatives [J].
Xia, Ji-Bao ;
You, Shu-Li .
ORGANOMETALLICS, 2007, 26 (20) :4869-4871
[68]   Pd(II)-Catalyzed C-H Activation/Aryl-Aryl Coupling of Phenol Esters [J].
Xiao, Bin ;
Fu, Yao ;
Xu, Jun ;
Gong, Tian-Jun ;
Dai, Jian-Jun ;
Yi, Jun ;
Liu, Lei .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (02) :468-+
[69]   Pd-Catalyzed Arylation/Oxidation of Benzylic C-H Bond [J].
Xie, Yongju ;
Yang, Yuzhu ;
Huang, Lehao ;
Zhang, Xunbin ;
Zhang, Yuhong .
ORGANIC LETTERS, 2012, 14 (05) :1238-1241
[70]   Organopalladium(IV) chemistry [J].
Xu, Ling-Min ;
Li, Bi-Jie ;
Yang, Zhen ;
Shi, Zhang-Jie .
CHEMICAL SOCIETY REVIEWS, 2010, 39 (02) :712-733
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