The Heck Reaction Applied to 1,3-and 1,2-Unsaturated Derivatives, a Way towards Molecular Complexity

被引:57
作者
Deagostino, Annamaria [1 ]
Prandi, Cristina [1 ]
Tabasso, Silvia [1 ]
Venturello, Paolo [1 ]
机构
[1] Univ Turin, Dipartimento Chim Gen & Chim Organ, I-10125 Turin, Italy
关键词
Mizoroki-Heck reaction; palladium; 1,2-dienes; 1,3-dienes; PALLADIUM-CATALYZED HETEROANNULATION; FUNCTIONALLY-SUBSTITUTED ARYL; ALDER CASCADE PROCESSES; EFFICIENT CATALYSTS; CYCLIZATION; ALLENES; CARBON; PALLADACYCLES; INDOLE-2,3-QUINODIMETHANES; CARBOANNULATION;
D O I
10.3390/molecules15042667
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
This review is an overview of the last ten years' use of the Mizoroki-Heck coupling applied to 1,2- and 1,3-dienes. Since both these systems form pi-allyl palladium intermediates in Pd(0) coupling, they show particular chemical behavior. Many examples of 1,2-dienes Heck reactions are presented. 1,2-Dienes are important substrates because of their high reactivity that makes them useful building blocks for the synthesis of biologically relevant structures.
引用
收藏
页码:2667 / 2685
页数:19
相关论文
共 40 条
[1]   Palladium-Catalyzed Domino Carbopalladation/5-exo-Allylic Amination of α-Amino Allenamides: An Efficient Entry to Enantiopure Imidazolidinones [J].
Beccalli, Egle M. ;
Broggini, Gianluigi ;
Clerici, Francesca ;
Galli, Simona ;
Kammerer, Claire ;
Rigamonti, Micol ;
Sottocornola, Silvia .
ORGANIC LETTERS, 2009, 11 (07) :1563-1566
[2]   Heck reaction on 1-alkoxy-1,3-dienes in ionic liquids: A superior medium for the regioselective arylation of the conjugated dienic system [J].
Beccaria, Luca ;
Deagostino, Annamaria ;
Prandi, Cristina ;
Zavattaro, Chiara ;
Venturello, Paolo .
SYNLETT, 2006, (18) :2989-2992
[3]   Three-component Heck-Diels-Alder cascade processes involving alkylallenes, aryl iodides and dienophiles [J].
Brown, S ;
Grigg, R ;
Hinsley, J ;
Korn, S ;
Sridharan, V ;
Uttley, MD .
TETRAHEDRON, 2001, 57 (52) :10347-10355
[4]   Palladium-catalyzed coupling of allenylphosphonates, phenylallenes, and allenyl esters: Remarkable salt effect and routes to novel benzofurans and isocoumarins [J].
Chakravarty, Manab ;
Swamy, K. C. Kumara .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (24) :9128-9138
[5]   Incomplete global integration and regional knowledge-intensive service industries [J].
Chen, YM .
SERVICE INDUSTRIES JOURNAL, 2006, 26 (02) :223-248
[6]   3-Component palladium-indium mediated diastereoselective cascade allylation of imines with allenes and aryl iodides [J].
Cooper, IR ;
Grigg, R ;
MacLachlan, WS ;
Thornton-Pett, M ;
Sridharan, V .
CHEMICAL COMMUNICATIONS, 2002, (13) :1372-1373
[7]   LIC-KOR promoted formation of conjugated dienes as useful building blocks for palladium-catalyzed syntheses [J].
Deagostino, A ;
Migliardi, M ;
Occhiato, EG ;
Prandi, C ;
Zavattaro, C ;
Venturello, P .
TETRAHEDRON, 2005, 61 (13) :3429-3436
[8]   Palladium-catalyzed heck reaction on 1-alkoxy-1,3-dienes:: A regioselective γ-arylation of α,β-unsaturated carbonyl compounds [J].
Deagostino, A ;
Prandi, C ;
Venturello, P .
ORGANIC LETTERS, 2003, 5 (21) :3815-3817
[9]   Palladium-catalysed Heck reaction on 1,2-dien-1-ols: a stereoselective synthesis of α-arylated α,β-unsaturated aldehydes [J].
Deagostino, Annamaria ;
Prandi, Cristina ;
Toppino, Antonio ;
Venturello, Paolo .
TETRAHEDRON, 2008, 64 (45) :10344-10349
[10]   8-Methylquinoline palladacycles: stable and efficient catalysts for carbon-carbon bond formation [J].
Evans, P ;
Hogg, P ;
Grigg, R ;
Nurnabi, M ;
Hinsley, J ;
Sridharan, V ;
Suganthan, S ;
Korn, S ;
Collard, S ;
Muir, JE .
TETRAHEDRON, 2005, 61 (41) :9696-9704