Strain-Promoted Oxidative Annulation of Arynes and Cyclooctynes with Benzamides: Palladium-Catalyzed C-H/N-H Activation for the Synthesis of N-Heterocycles

被引:92
作者
Peng, Xianglong [1 ]
Wang, Weiguo [1 ]
Jiang, Chao [1 ]
Sun, Di [1 ]
Xu, Zhenghu [1 ]
Tung, Chen-Ho [1 ]
机构
[1] Shandong Univ, Sch Chem & Chem Engn, Key Lab Colloid & Interface Chem, Educ Minist, Jinan 250100, Peoples R China
关键词
FUSED POLYCYCLIC AROMATICS; HIGHLY EFFICIENT ROUTE; METAL RELAY CATALYSIS; MOLECULAR-OXYGEN; INDOLE SYNTHESIS; BORONIC ACIDS; ARYL HALIDES; DEHYDROGENATIVE ANNULATION; INTRAMOLECULAR AMINATION; ISOQUINOLONE SYNTHESIS;
D O I
10.1021/ol5025426
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Strained alkynes include arynes and cyclooctynes reacted with N-methoxyamides through palladium-catalyzed C-H/N-H activation for the first time. A variety of important N-heterocycles such as phenanthridinones and isoquinolones were constructed in one step with high efficiency.
引用
收藏
页码:5354 / 5357
页数:4
相关论文
共 102 条
[81]   Indole Synthesis via Rhodium Catalyzed Oxidative Coupling of Acetanilides and Internal Alkynes [J].
Stuart, David R. ;
Bertrand-Laperle, Megan ;
Burgess, Kevin M. N. ;
Fagnou, Keith .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (49) :16474-+
[82]   A Comprehensive History of Arynes in Natural Product Total Synthesis [J].
Tadross, Pamela M. ;
Stoltz, Brian M. .
CHEMICAL REVIEWS, 2012, 112 (06) :3550-3577
[83]   Re/Mg Bimetallic Tandem Catalysis for [4+2] Annulation of Benzamides and Alkynes via C-H/N-H Functionalization [J].
Tang, Qiuzheng ;
Xia, Dexin ;
Jin, Xiqing ;
Zhang, Qing ;
Sun, Xiao-Qiang ;
Wang, Congyang .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (12) :4628-4631
[84]   Pd(II)-catalyzed cross-coupling of sp3 C-H bonds with sp2 and sp3 boronic acids using air as the oxidant [J].
Wang, Dong-Hui ;
Wasa, Masayuki ;
Giri, Ramesh ;
Yu, Jin-Quan .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (23) :7190-+
[85]   One-Pot Formation of C-C and C-N Bonds through Palladium-Catalyzed Dual C-H Activation: Synthesis of Phenanthridinones [J].
Wang, Guan-Wu ;
Yuan, Ting-Ting ;
Li, Dan-Dan .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (06) :1380-1383
[86]   Mild Rh(III)-Catalyzed C-H Activation and Annulation with Alkyne MIDA Boronates: Short, Efficient Synthesis of Heterocyclic Boronic Acid Derivatives [J].
Wang, Honggen ;
Grohmann, Christoph ;
Nimphius, Corinna ;
Glorius, Frank .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (48) :19592-19595
[87]   Mild Rhodium(III)-Catalyzed C-H Activation and Intermolecular Annulation with Allenes [J].
Wang, Honggen ;
Glorius, Frank .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (29) :7318-7322
[88]   Palladium-Catalyzed Oxidative Cycloaddition through C-H/N-H Activation: Access to Benzazepines [J].
Wang, Lei ;
Huang, Jiayao ;
Peng, Shiyong ;
Liu, Hui ;
Jiang, Xuefeng ;
Wang, Jian .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (06) :1768-1772
[89]   Synthesis of 1-Aminoisoquinolines via Rh(III)-Catalyzed Oxidative Coupling [J].
Wei, Xiaohong ;
Zhao, Miao ;
Du, Zhengyin ;
Li, Xingwei .
ORGANIC LETTERS, 2011, 13 (17) :4636-4639
[90]   Synthesis of indolo[1,2-f]phenanthridines from palladium-catalyzed reactions of arynes [J].
Xie, Chunsong ;
Zhang, Yuhong ;
Huang, Zedu ;
Xu, Peixin .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (14) :5431-5434