Ortho C-H Acylation of Aryl Iodides by Palladium/Norbornene Catalysis

被引：160
作者：
Dong, Zhe [1 ]
Wang, Jianchun [1 ]
Ren, Zhi [1 ]
Dong, Guangbin [1 ]
机构：
[1] Univ Texas Austin, Dept Chem, Austin, TX 78712 USA
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2015年 / 54卷 / 43期
关键词：
acylation; arenes; C-H activation; heterocycles; palladium; CROSS-COUPLING REACTIONS; CARBOXYLIC ANHYDRIDES; PALLADIUM; KETONES; NORBORNENE; ACTIVATION; ARYLATION; SEQUENCE; INDOLES; CASCADE;
D O I：
10.1002/anie.201506397
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Reported herein is a palladium/norbornene-catalyzed ortho-arene acylation of aryl iodides by a Catellani-type C-H functionalization. This transformation is enabled by isopropyl carbonate anhydrides, which serve as both an acyl cation equivalent and a hydride source.
引用
收藏
页码：12664 / 12668
页数：5
相关论文
共 101 条
[41]   Palladium-Catalyzed Acylation of sp2 C-H bond: Direct Access to Ketones from Aldehydes [J].
Jia, Xiaofei ;
Zhang, Shouhui ;
Wang, Wenhui ;
Luo, Fang ;
Cheng, Jiang .
ORGANIC LETTERS, 2009, 11 (14) :3120-3123
[42]   Pd(II)-Catalyzed Regioselective 2-Alkylation of Indoles via a Norbornene-Mediated C-H Activation: Mechanism and Applications [J].
Jiao, Lei ;
Herdtweck, Eberhardt ;
Bach, Thorsten .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (35) :14563-14572
[43]   Palladium-Catalyzed Direct 2-Alkylation of Indoles by Norbornene-Mediated Regioselective Cascade C-H Activation [J].
Jiao, Lei ;
Bach, Thorsten .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (33) :12990-12993
[44]   Synthesis of unsymmetrical ketones by palladium-catalyzed cross-coupling reaction of carboxylic anhydrides with organoboron compounds [J].
Kakino, R ;
Yasumi, S ;
Shimizu, I ;
Yamamoto, A .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2002, 75 (01) :137-148
[45]  
Lautens M, 2000, ANGEW CHEM INT EDIT, V39, P1045, DOI 10.1002/(SICI)1521-3773(20000317)39:6<1045::AID-ANIE1045>3.0.CO
[46]  
2-Q
[47]  
lautens m, 2000, ANGEW CHE, V112, P1087
[48]   Nonenzymatic Dynamic Kinetic Resolution of Secondary Alcohols via Enantioselective Acylation: Synthetic and Mechanistic Studies [J].
Lee, Sarah Yunmi ;
Murphy, Jaclyn M. ;
Ukai, Atsushi ;
Fu, Gregory C. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (36) :15149-15153
[49]   Redox-Neutral Palladium-Catalyzed C-H Functionalization To Form lsoindolinones with Carboxylic Acids or Anhydrides as Readily Available Starting Materials [J].
Liang, Hong-Wen ;
Ding, Wei ;
Jiang, Kun ;
Shuai, Li ;
Yuan, Yi ;
Wei, Ye ;
Chen, Ying-Chun .
ORGANIC LETTERS, 2015, 17 (11) :2764-2767
[50]  
Liu H., 2012, Angew. Chem, V124, P9984, DOI DOI 10.1071/CH06250
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