Ruthenium-Catalyzed Alkyne Annulations with Substituted 1H-Pyrazoles by C-H/N-H Bond Functionalizations

被引：84
作者：
Ma, Wenbo [1 ]
Graczyk, Karolina [1 ]
Ackermann, Lutz [1 ]
机构：
[1] Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany
来源：
ORGANIC LETTERS | 2012年 / 14卷 / 24期
基金：
欧洲研究理事会;
关键词：
OXIDATIVE ALKENYLATION; ACTIVATION; PALLADIUM; PHENYLAZOLES; CYCLIZATION; ARYLATIONS; MECHANISM; CLEAVAGE; INDOLES; ACIDS;
D O I：
10.1021/ol303083n
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Cationic ruthenium(II) complexes allowed for highly efficient oxidative annulations of aryl- and alkyl-substituted alkynes by 5-aryl-1H-pyrazoles. The C-H/N-H bond functionalization strategy furthermore proved applicable to the high-yielding activation of heteroaryl as well as alkenyl C-H bonds.
引用
收藏
页码：6318 / 6321
页数：4
相关论文
共 55 条
[1]   Catalytic arylations with challenging substrates: From air-stable HASPO preligands to indole syntheses and C-H-bond functionalizations [J].
Ackermann, Lutz .
SYNLETT, 2007, (04) :507-526
[2]   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
[3]   Cationic Ruthenium(II) Catalysts for Oxidative C-H/N-H Bond Functionalizations of Anilines with Removable Directing Group: Synthesis of Indoles in Water [J].
Ackermann, Lutz ;
Lygin, Alexander V. .
ORGANIC LETTERS, 2012, 14 (03) :764-767
[4]   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
[5]   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
[6]   Ruthenium-Catalyzed Oxidative C-H Bond Alkenylations in Water: Expedient Synthesis of Annulated Lactones [J].
Ackermann, Lutz ;
Pospech, Jola .
ORGANIC LETTERS, 2011, 13 (16) :4153-4155
[7]   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
[8]   Ruthenium-Catalyzed Oxidative Synthesis of 2-Pyridones through C-H/N-H Bond Functionalizations [J].
Ackermann, Lutz ;
Lygin, Alexander V. ;
Hofmann, Nora .
ORGANIC LETTERS, 2011, 13 (12) :3278-3281
[9]   Carboxylate-Assisted Transition-Metal-Catalyzed C-H Bond Functionalizations: Mechanism and Scope [J].
Ackermann, Lutz .
CHEMICAL REVIEWS, 2011, 111 (03) :1315-1345
[10]   Air-Stable Bifunctional HASPO Preligands for Metal-Catalyzed Cross-Couplings and Direct C-H Bond Arylations [J].
Ackermann, Lutz .
ISRAEL JOURNAL OF CHEMISTRY, 2010, 50 (5-6) :652-663
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