Functionalization of Csp3-H and Csp2-H Bonds: Synthesis of Spiroindenes by Enolate-Directed Ruthenium-Catalyzed Oxidative Annulation of Alkynes with 2-Aryl-1,3-dicarbonyl Compounds

被引:119
作者
Chidipudi, Suresh Reddy [1 ]
Khan, Imtiaz [1 ]
Lam, Hon Wai [1 ]
机构
[1] Univ Edinburgh, Sch Chem, EaStCHEM, Edinburgh EH9 3JJ, Midlothian, Scotland
基金
英国工程与自然科学研究理事会;
关键词
annulation; C-H functionalization; oxidation; ruthenium; synthetic methods; C-H ACTIVATION; INTERNAL ALKYNES; REGIOSELECTIVE SYNTHESIS; AROMATIC KETIMINES; ARYL KETONES; PALLADIUM; DERIVATIVES; CLEAVAGE; INDOLES; INDENE;
D O I
10.1002/anie.201207170
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Ru(de) awakening: The synthesis of carbocycles by the ruthenium-catalyzed oxidative annulation of alkynes with 2-aryl cyclic 1,3-dicarbonyl substrates is described. Proceeding by the functionalization of C sp 3-H and C sp 2-H bonds, and the formation of an all-carbon quaternary center, the reaction provides a diverse range of spiroindenes in good yields with high levels of regioselectivity. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:12115 / 12119
页数:5
相关论文
共 77 条
[1]  
Ackermann L., 2009, ANGEW CHEM, V121, P9976, DOI DOI 10.1002/ANGE.200902996
[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 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
[7]   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
[8]   Carboxylate-Assisted Transition-Metal-Catalyzed C-H Bond Functionalizations: Mechanism and Scope [J].
Ackermann, Lutz .
CHEMICAL REVIEWS, 2011, 111 (03) :1315-1345
[9]   Ruthenium-Catalyzed Direct Arylations Through C-H Bond Cleavages [J].
Ackermann, Lutz ;
Vicente, Ruben .
C-H ACTIVATION, 2010, 292 :211-229
[10]   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