Ruthenium-catalyzed oxidative alkyne annulation by C-H activation on ketimines

被引:34
作者
Li, Jie [1 ]
Ackermann, Lutz [1 ]
机构
[1] Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany
基金
欧洲研究理事会;
关键词
C-H activation; Isoquinolines; Heterocycles; Ketimines; Multicatalysis; Ruthenium; ONE-POT SYNTHESIS; N BOND FORMATION; ISOQUINOLINIUM SALTS; FUNCTIONALIZATION; PYRIDINES; CYCLIZATION; PALLADIUM; KETOXIMES; IMINES; RH;
D O I
10.1016/j.tet.2013.10.003
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Carboxylate assistance allowed for ruthenium(II)-catalyzed oxidative alkyne annulations by ketimines under an ambient atmosphere of air. The ruthenium catalyst outperformed representative rhodium and palladium complexes, and provided versatile access to differently decorated 1-methylene-1,2-dihydroisoquinolines in a highly step- and atom-economical manner. Detailed mechanistic studies provided evidence for an initial reversible C-H bond activation event. (C) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3342 / 3348
页数:7
相关论文
共 52 条
[1]   Versatile Synthesis of Isocoumarins and α-Pyrones by Ruthenium-Catalyzed Oxidative C-H/O-H Bond Cleavages [J].
Ackermann, Lutz ;
Pospech, Jola ;
Graczyk, Karolina ;
Rauch, Karsten .
ORGANIC LETTERS, 2012, 14 (03) :930-933
[2]   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
[3]   Ruthenium-catalyzed aerobic oxidative coupling of alkynes with 2-aryl-substituted pyrroles [J].
Ackermann, Lutz ;
Wang, Lianhui ;
Lygin, Alexander V. .
CHEMICAL SCIENCE, 2012, 3 (01) :177-180
[4]   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
[5]   Carboxylate-Assisted Transition-Metal-Catalyzed C-H Bond Functionalizations: Mechanism and Scope [J].
Ackermann, Lutz .
CHEMICAL REVIEWS, 2011, 111 (03) :1315-1345
[6]   Metal-catalyzed direct alkylations of (hetero)arenes via C-H bond cleavages with unactivated alkyl halides [J].
Ackermann, Lutz .
CHEMICAL COMMUNICATIONS, 2010, 46 (27) :4866-4877
[7]   Transition-Metal-Catalyzed Direct Arylation of (Hetero)Arenes by C-H Bond Cleavage [J].
Ackermann, Lutz ;
Vicente, Ruben ;
Kapdi, Anant R. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (52) :9792-9826
[8]  
Alajarín R, 2011, MODERN HETEROCYCLIC CHEMISTRY, VOL 4, P1527
[9]   Aryl-aryl bond formation by transition-metal-catalyzed direct arylation [J].
Alberico, Dino ;
Scott, Mark E. ;
Lautens, Mark .
CHEMICAL REVIEWS, 2007, 107 (01) :174-238
[10]  
[Anonymous], ACC CHEM RES