Palladium-Catalyzed Asymmetric Reductive Heck Reaction of Aryl Halides

被引：139
作者：
Yue, Guizhou [1 ,2 ]
Lei, Kaining [1 ]
Hirao, Hajime [1 ]
Zhou, Jianrong [1 ]
机构：
[1] Nanyang Technol Univ, Sch Phys & Math Sci, Div Chem & Biol Chem, Singapore 637371, Singapore
[2] Sichuan Agr Univ, Coll Sci, Yaan 625014, Sichuan, Peoples R China
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2015年 / 54卷 / 22期
关键词：
asymmetric catalysis; hydrogen bonding; olefins; palladium; synthetic methods; CENTER-DOT-O; CHIRAL 3-SUBSTITUTED INDANONES; TRANSITION-METAL CATALYSIS; CONJUGATE ADDITION; ARYLBORONIC ACIDS; ENANTIOSELECTIVE SYNTHESIS; HYDROGEN-BOND; ALPHA; BETA-UNSATURATED KETONES; ARYLPALLADIUM COMPLEXES; UNACTIVATED ALKENES;
D O I：
10.1002/anie.201501712
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Asymmetric reductive Heck reaction of aryl halides is realized in high stereoselectivity. Hydrogen-bond donors, trialkylammonium salts in a glycol solvent, were used to promote halide dissociation from neutral arylpalladium complexes to access cationic, stereoselective pathways.
引用
收藏
页码：6531 / 6535
页数：5
相关论文
共 105 条
[1]   Enantioselective copper-catalyzed conjugate addition and allylic substitution reactions [J].
Alexakis, A. ;
Backvall, J. E. ;
Krause, N. ;
Pamies, O. ;
Dieguez, M. .
CHEMICAL REVIEWS, 2008, 108 (08) :2796-2823
[2]   Rate and mechanism of the heck reactions of arylpalladium complexes ligated by a bidentate P,P ligand with an electron-rich alkene (isobutyl vinyl ether) [J].
Amatore, Christian ;
Godin, Beatrice ;
Jutand, Anny ;
Lemaitre, Frederic .
ORGANOMETALLICS, 2007, 26 (07) :1757-1761
[3]   Rate and mechanism of the reaction of alkenes with aryl palladium complexes ligated by a bidentate PP ligand in Heck reactions [J].
Amatore, Christian ;
Godin, Beatrice ;
Jutand, Anny ;
Lemaitre, Frederic .
CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (07) :2002-2011
[4]   CONJUGATE ADDITION VS VINYLIC SUBSTITUTION IN PALLADIUM-CATALYZED REACTION OF ARYL HALIDES WITH BETA-SUBSTITUTED-ALPHA,BETA-ENONES AND BETA-SUBSTITUTED-ALPHA,BETA-ENALS [J].
AMORESE, A ;
ARCADI, A ;
BERNOCCHI, E ;
CACCHI, S ;
CERRINI, S ;
FEDELI, W ;
ORTAR, G .
TETRAHEDRON, 1989, 45 (03) :813-828
[5]   DEVELOPMENT OF A RECEPTOR-INTERACTION MODEL FOR SEROTONIN 5-HT2 RECEPTOR ANTAGONISTS - PREDICTING SELECTIVITY WITH RESPECT TO DOPAMINE D-2 RECEPTORS [J].
ANDERSEN, K ;
LILJEFORS, T ;
GUNDERTOFTE, K ;
PERREGAARD, J ;
BOGESO, KP .
JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (07) :950-962
[6]  
[Anonymous], ANGEW CHEM, DOI DOI 10.1002/ANGE.200300579
[7]  
[Anonymous], 2015, ANGEW CHEM
[8]  
[Anonymous], ANGEW CHEM
[9]  
[Anonymous], 2006, ANGEW CHEM INT EDIT
[10]   Catalytic enantioselective Negishi reactions of racemic secondary benzylic halides [J].
Arp, FO ;
Fu, GC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (30) :10482-10483
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