Palladium-catalyzed electrophilic allylation reactions via bis(allyl)palladium complexes and related intermediates

被引:70
作者
Szabó, KJ [1 ]
机构
[1] Stockholm Univ, Arrhenius Lab, Dept Organ Chem, S-10691 Stockholm, Sweden
关键词
allylation; density functional calculations; electrophilic substitution; homogeneous catalysis; palladium;
D O I
10.1002/chem.200400261
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The synthetic scope of the allyl-palladium chemistry can be extended to involve electrophilic reagents. The greatest challange in these reactions is the catalytic generation of an allyl-palladium intermediate incorporating a nucleophilic allyl moiety. A vast majority of the published reactions that involve palladium-catalyzed allylation of electrophiles proceed via bis(allyl)-palladium intermediates. The eta(1)-moiety of the bis(allyl)-palladium intermediates reacts with electrophiles, including aldehydes, imines, or Michael acceptors. Recently, catalytic electrophilic allylations via monoallylpalladium complexes were also presented by employment of so-called "pincer complex" catalysts.
引用
收藏
页码:5268 / 5275
页数:8
相关论文
共 55 条
[1]  
Albrecht M., 2001, ANGEW CHEM, V113, P3866, DOI DOI 10.1002/1521-3773(20011015)113:20<3866::AID-ANGE3866>3.0.C0
[2]  
2-Y
[3]  
[Anonymous], ORGANOPALLADIUM CHEM
[4]   Palladium bis(phosphinite) 'PCP'-pincer complexes and their application as catalysts in the Suzuki reaction [J].
Bedford, RB ;
Draper, SM ;
Scully, PN ;
Welch, SL .
NEW JOURNAL OF CHEMISTRY, 2000, 24 (10) :745-747
[5]   INTERMEDIATES IN THE PALLADIUM-CATALYZED REACTIONS OF 1,3-DIENES .2. PREPARATION AND STRUCTURE OF (ETA-1,ETA-3-OCTADIENEDIYL)PALLADIUM COMPLEXES [J].
BENN, R ;
JOLLY, PW ;
MYNOTT, R ;
RASPEL, B ;
SCHENKER, G ;
SCHICK, KP ;
SCHROTH, G .
ORGANOMETALLICS, 1985, 4 (11) :1945-1953
[6]   Chiral bis-π-allylpalladium complex catalyzed asymmetric allylation of imines:: Enhancement of the enantioselectivity and chemical yield in the presence of water [J].
Fernandes, RA ;
Stimac, A ;
Yamamoto, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (46) :14133-14139
[7]   Palladium-catalyzed carboxylative coupling of allylstannanes and allyl halides [J].
Franks, RJ ;
Nicholas, KM .
ORGANOMETALLICS, 2000, 19 (08) :1458-1460
[8]  
GODLESKI SA, 1991, NUCLEOPHILES ALLYL M, V4
[9]   SPECIFIC ALLYLIC ALLYLIC COUPLING PROCEDURES EFFECTED BY LIGAND-INDUCED ELIMINATION FROM DI(ALLYLIC)PALLADIUM SPECIES [J].
GOLIASZEWSKI, A ;
SCHWARTZ, J .
TETRAHEDRON, 1985, 41 (24) :5779-5789
[10]   CARBON CARBON BOND FORMATION BY INDUCED ELIMINATION FROM UNSYMMETRICALLY SUBSTITUTED (ALLYL)(ALLYL') PALLADIUM COMPLEXES [J].
GOLIASZEWSKI, A ;
SCHWARTZ, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (17) :5028-5030