Practical synthesis of multifunctional compounds through Pd/C-catalyzed coupling reactions

被引:31
作者
Seki, Masahiko [1 ]
机构
[1] Tanabe Seiyaku Co Ltd, Yodogawa Ku, Osaka 5328505, Japan
关键词
palladium; palladium on activated carbon; heterogeneous catalyst; catalysis; cross coupling; Heck coupling; Suzuki-Miyaura coupling; Sonogashira coupling; Fukuyama coupling; cyanation;
D O I
10.5059/yukigoseikyokaishi.64.853
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Practical approaches to multifunctional compounds through palladium on activated carbon (Pd/C)-catalyzed Heck, Suzuki and Miyaura, Sonogashira, Fukuyama coupling and others are discussed. Correlation of the properties of the heterogeneous catalysts, e.g., palladium distribution and reduction degree, with the efficiency of the reaction has been observed and largely depends upon the type of the reactions. A critical role of the solid support is supposed to help palladium highly disperse on the solid surface to form active Pd complex without aggregating to inactive palladium black. The reactions are so practical as to be applied to cost-effective large-scale production of multifunctional intermediates for drug-synthesis.
引用
收藏
页码:853 / 866
页数:14
相关论文
共 124 条
[1]   The polymer incarcerated method for the preparation of highly active heterogeneous palladium catalysts [J].
Akiyama, R ;
Kobayashi, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (12) :3412-3413
[2]   REGIOCHEMISTRY OF PALLADIUM-CATALYZED ARYLATION REACTIONS OF ENOL ETHERS - ELECTRONIC CONTROL OF SELECTION FOR ALPHA-ARYLATION OR BETA-ARYLATION [J].
ANDERSSON, CM ;
HALLBERG, A ;
DAVES, GD .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (16) :3529-3536
[3]   A mild and versatile method for palladium-catalyzed cross-coupling of aryl halides in water and surfactants [J].
Arcadi, A ;
Cerichelli, G ;
Chiarini, M ;
Correa, M ;
Zorzan, D .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (20) :4080-4086
[4]   Suzuki coupling of aryl chlorides with phenylboronic acid in water, using microwave heating with simultaneous cooling [J].
Arvela, RK ;
Leadbeater, NE .
ORGANIC LETTERS, 2005, 7 (11) :2101-2104
[5]   An oxime-carbapalladacycle complex covalently anchored to silica as an active and reusable heterogeneous catalyst for Suzuki cross-coupling in water [J].
Baleizao, C ;
Corma, A ;
García, H ;
Leyva, A .
CHEMICAL COMMUNICATIONS, 2003, (05) :606-607
[6]   The pyridinium reduction route to alkaloids:: a synthesis of (±)-tashiromine [J].
Bates, RW ;
Boonsombat, J .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (07) :654-656
[7]   Silica-supported imine palladacycles - recyclable catalysts for the Suzuki reaction? [J].
Bedford, RB ;
Cazin, CSJ ;
Hursthouse, MB ;
Light, ME ;
Pike, KJ ;
Wimperis, S .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 633 (1-2) :173-181
[8]   A new improved palladium-catalyzed amidocarbonylation [J].
Beller, M ;
Moradi, WA ;
Eckert, M ;
Neumann, H .
TETRAHEDRON LETTERS, 1999, 40 (24) :4523-4526
[9]   Palladium-catalyzed amidocarbonylation - A new, efficient synthesis of N-acyl amino acids [J].
Beller, M ;
Eckert, M ;
Vollmuller, F ;
Bogdanovic, S ;
Geissler, H .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (13-14) :1494-1496
[10]   A new class of catalysts with superior activity and selectivity for amidocarbonylation reactions [J].
Beller, M ;
Eckert, MK ;
Vollmuller, F .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1998, 135 (01) :23-33