Recent Advances in Palladium-Catalyzed Cascade Cyclizations

被引:241
作者
Vlaar, Tjostil [1 ]
Ruijter, Eelco [1 ]
Orru, Romano V. A. [1 ]
机构
[1] Vrije Univ Amsterdam, Dept Chem & Pharmaceut Sci, NL-1081 HV Amsterdam, Netherlands
关键词
cascade reactions; catalysis; cyclization; multicomponent reactions; palladium; tandem reactions; ANION CAPTURE PROCESSES; RING EXPANSION REACTION; SEQUENTIAL HOMOBIMETALLIC CATALYSIS; EMPLOYING CARBON-MONOXIDE; N-ANNULATION ROUTE; ONE-POT SYNTHESIS; 2,3-DISUBSTITUTED INDOLES; PROPARGYLIC CARBONATES; NITROGEN-HETEROCYCLES; COUPLING REACTIONS;
D O I
10.1002/adsc.201000979
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
The importance of palladium-catalyzed cross coupling reactions in contemporary organic synthesis is undisputed and underlined by the Nobel Prize for Chemistry in 2010. In addition to the highly efficient cross coupling reactions for single C-C bond construction, palladium-catalyzed cascade processes involving multiple bond formations have emerged in recent years as valuable tools for the rapid synthesis of complex molecular scaffolds. This review presents an overview of the most relevant developments in this field, with a focus on the generation of diverse poly-and heterocyclic scaffolds. The generally well understood reactivity of palladium has allowed the discovery of many intriguing novel cascade processes, and the creativity of the synthetic community will undoubtedly lead to many more discoveries in the future.
引用
收藏
页码:809 / 841
页数:33
相关论文
共 157 条
[1]   General and efficient indole syntheses based on catalytic amination reactions [J].
Ackermann, L .
ORGANIC LETTERS, 2005, 7 (03) :439-442
[2]   Asymmetric synthesis of avenaciolide via cascade palladium catalysed cyclisation-carbonylation of bromodienes [J].
Aggarwal, VK ;
Davies, PW ;
Schmidt, AT .
CHEMICAL COMMUNICATIONS, 2004, (10) :1232-1233
[3]   A palladium catalysed cyclisation-carbonylation of bromodienes:: control in carbonylation over facile β-hydride elimination [J].
Aggarwal, VK ;
Davies, PW ;
Moss, WO .
CHEMICAL COMMUNICATIONS, 2002, (09) :972-973
[4]  
[Anonymous], ANGEW CHEM
[5]   Palladium catalysed queuing processes. Part 2: Termolecular cyclization-anion capture employing carbon monoxide as a relay switch with in situ generated vinylstannanes [J].
Anwar, U ;
Casaschi, A ;
Grigg, R ;
Sansano, JM .
TETRAHEDRON, 2001, 57 (07) :1361-1367
[6]   Palladium-Catalyzed Domino C,N-Coupling/Carbonylation/Suzuki Coupling Reaction: An Efficient Synthesis of 2-Aroyl-/Heteroaroylindoles [J].
Arthuis, Martin ;
Pontikis, Renee ;
Florent, Jean-Claude .
ORGANIC LETTERS, 2009, 11 (20) :4608-4611
[7]   Cyclopropyl building blocks for organic synthesis, 131. Palladium-catalyzed bicyclization with carbonyl insertion of alkenyl-tethered propargyl carbonates towards a scalable synthesis of various 2-(bicyclo[3.1.0]hex-1-yl) acrylates [J].
Bagutski, Viktor ;
Moszner, Norbert ;
Zeuner, Frank ;
Fischer, Urs Karl ;
de Meijere, Armin .
ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (15) :2133-2147
[8]   Catalysts for Suzuki-Miyaura coupling processes: Scope and studies of the effect of ligand structure [J].
Barder, TE ;
Walker, SD ;
Martinelli, JR ;
Buchwald, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (13) :4685-4696
[9]   Cascade alkenyl amination/heck reaction promoted by a bifunctional palladium catalyst:: A novel one-pot synthesis of indoles from o-haloanilines and alkenyl halides [J].
Barluenga, J ;
Fernández, MA ;
Aznar, F ;
Valdés, C .
CHEMISTRY-A EUROPEAN JOURNAL, 2005, 11 (08) :2276-2283
[10]   Recent Advances in the Synthesis of Indole and Quinoline Derivatives through Cascade Reactions [J].
Barluenga, Jose ;
Rodriguez, Felix ;
Fananas, Francisco J. .
CHEMISTRY-AN ASIAN JOURNAL, 2009, 4 (07) :1036-1048