Co(III)-Catalyzed [4+1] Annulation of Amides with Allenes via C-H Activation

被引:29
作者
Boobalan, Ramadoss [1 ]
Santhoshkumar, Rajagopal [1 ]
Cheng, Chien-Hong [1 ]
机构
[1] Natl Tsing Hua Univ, Dept Chem, Hsinchu 30013, Taiwan
关键词
Cobalt; Allenes; Annulation; Amides; C-H Activation; REGIOSELECTIVE INTERMOLECULAR ANNULATION; CATALYZED OXIDATIVE ANNULATION; BOND FUNCTIONALIZATION; CARBOXYLIC-ACIDS; DIRECTING GROUPS; ALKYNES; ISOQUINOLINES; SULFONAMIDES; REACTIVITY; BENZAMIDES;
D O I
10.1002/adsc.201801335
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A Co(III)-catalyzed [4+1] annulation of amides with allenes to synthesize isoindolone and 1,5-dihydro-pyrrol-2-one derivatives is reported. A wide range of aromatic and vinylic amides react with allenes to give the corresponding annulation products in good to excellent yields. The mechanistic studies strongly support that the catalytic reaction proceeds through an amide-directed C-H activation, followed by carbocobaltation of allene, -hydride elimination, and an intramolecular 1,2-hydroamination.
引用
收藏
页码:1140 / 1145
页数:6
相关论文
共 71 条
[1]   Carboxylate-Assisted Ruthenium-Catalyzed Alkyne Annulations by C-H/Het-H Bond Functionalizations [J].
Ackermann, Lutz .
ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (02) :281-295
[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]   The conversion of allenes to strained three-membered heterocycles [J].
Adams, C. S. ;
Weatherly, C. D. ;
Burke, E. G. ;
Schomaker, J. M. .
CHEMICAL SOCIETY REVIEWS, 2014, 43 (09) :3136-3163
[4]   On the Antibiotic and Antifungal Activity of Pestalone, Pestalachloride A, and Structurally Related Compounds [J].
Augner, Daniel ;
Krut, Oleg ;
Slavov, Nikolay ;
Gerbino, Dario C. ;
Sahl, Hans-Georg ;
Benting, Juergen ;
Nising, Carl F. ;
Hillebrand, Stefan ;
Kroenke, Martin ;
Schmalz, Hans-Guenther .
JOURNAL OF NATURAL PRODUCTS, 2013, 76 (08) :1519-1522
[5]   Access to Isoquinolin-1(2H)-ones and Pyridones by Cobalt-Catalyzed Oxidative Annulation of Amides with Allenes [J].
Boobalan, Ramadoss ;
Kuppusamy, Ramajayam ;
Santhoshkumar, Rajagopal ;
Gandeepan, Parthasarathy ;
Cheng, Chien-Hong .
CHEMCATCHEM, 2017, 9 (02) :273-277
[6]   Rhodium-Catalyzed (5+1) Annulations Between 2-Alkenylphenols and Allenes: A Practical Entry to 2,2-Disubstituted 2H-Chromenes [J].
Casanova, Noelia ;
Seoane, Andres ;
Mascarenas, Jose L. ;
Gulias, Moises .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (08) :2374-2377
[7]   Nickel Catalysts/N,N′-Bidentate Directing Groups: An Excellent Partnership in Directed C-H Activation Reactions [J].
Castro, Luis C. Misal ;
Chatani, Naoto .
CHEMISTRY LETTERS, 2015, 44 (04) :410-421
[8]   Formal [4+1] Annulation Reactions in the Synthesis of Carbocyclic and Heterocyclic Systems [J].
Chen, Jia-Rong ;
Hu, Xiao-Qiang ;
Lu, Liang-Qiu ;
Xiao, Wen-Jing .
CHEMICAL REVIEWS, 2015, 115 (11) :5301-5365
[9]   Cp*Co(III)-Catalyzed Coupling of Benzamides with α,β-Unsaturated Carbonyl Compounds: Preparation of Aliphatic Ketones and Azepinones [J].
Chirila, Paula G. ;
Adams, Joshua ;
Dirjal, Amir ;
Hamilton, Alex ;
Whiteoak, Christopher J. .
CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (14) :3584-3589
[10]   Weakly Coordinating Directing Groups for Ruthenium(II)-Catalyzed C-H Activation [J].
De Sarkar, Suman ;
Liu, Weiping ;
Kozhushkov, Sergei I. ;
Ackermann, Lutz .
ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (07) :1461-1479