Organocatalytic Oxidative Annulation of Benzamide Derivatives with Alkynes

被引:106
作者
Manna, Srimanta [1 ,2 ]
Antonchick, Andrey P. [1 ,2 ]
机构
[1] Max Planck Inst Mol Physiol, Abt Chem Biol, D-44227 Dortmund, Germany
[2] Tech Univ Dortmund, Fak Chem, D-44221 Dortmund, Germany
关键词
alkynes; annulation; heterocycles; hypervalent iodine; organocatalysis; C-H ACTIVATION; HYPERVALENT IODINE REAGENTS; N BOND FORMATION; ISOQUINOLINE ALKALOIDS; BETA-PHENYLETHYLAMINES; O BOND; COUPLING/CYCLIZATION; FUNCTIONALIZATION; STRATEGY; CYCLOADDITION;
D O I
10.1002/anie.201404222
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Organocatalytic annulation by functionalization of benzamide derivatives with alkynes has been developed. We report a new approach of cycloaddition under mild reaction conditions using simple catalysts, such as iodobenzene and peracetic acid, as oxidant. Those novel, mild reaction conditions provided a straightforward synthesis of isoquinolones with fast reaction rate. Notable selectivity in annulation of unsymmetrically disubstituted alkynes was demonstrated.
引用
收藏
页码:7324 / 7327
页数:4
相关论文
共 90 条
[1]   Ruthenium-Catalyzed C-H/N-O Bond Functionalization: Green Isoquinolone Syntheses in Water [J].
Ackermann, Lutz ;
Fenner, Sabine .
ORGANIC LETTERS, 2011, 13 (24) :6548-6551
[2]   Ruthenium-Catalyzed Oxidative Annulation by Cleavage of C-H/N-H Bonds [J].
Ackermann, Lutz ;
Lygin, Alexander V. ;
Hofmann, Nora .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (28) :6379-6382
[3]   Carboxylate-Assisted Transition-Metal-Catalyzed C-H Bond Functionalizations: Mechanism and Scope [J].
Ackermann, Lutz .
CHEMICAL REVIEWS, 2011, 111 (03) :1315-1345
[4]  
[Anonymous], 2012, Angew. Chem
[5]  
[Anonymous], 2012, ANGEW CHEM
[6]  
[Anonymous], 2014, Angew. Chem
[7]  
[Anonymous], 2012, ANGEW CHEM
[8]  
Antonchick A. P., 2011, ANGEW CHEM, V123, P8764
[9]  
Antonchick A. P., 2013, ANGEW CHEM, V125, P3349
[10]   Direct Selective Oxidative Cross-Coupling of Simple Alkanes with Heteroarenes [J].
Antonchick, Andrey P. ;
Burgmann, Lars .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (11) :3267-3271