Synthetic and mechanistic studies of the cycloisomerization and cyclization/hydrosilylation of functionalized dienes catalyzed by cationic palladium(II) complexes

被引：142

作者：

Widenhoefer, RA ^{[1
]}

机构：

[1] Duke Univ, PM Gross Chem Lab, Durham, NC 27708 USA

来源：

ACCOUNTS OF CHEMICAL RESEARCH | 2002年 / 35卷 / 10期

关键词：

D O I：

10.1021/ar010040n

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

This Account describes the development and mechanistic study of the cycloisomerization and cyclization/hydrosilylation of functionalized dienes catalyzed by cationic palladium (II), complexes. These transformations are characterized by good functional group compatibility, high regio- and stereoselectivity, and low air- and moisture-sensitivity. Mechanistic studies of palladium phenanthroline-catalyzed diene cycloisomerization and cyclization/hydrosilylation established mechanisms involving C-C bond formation via intramolecular carbometalation of an alkyl olefin chelate complex, which was directly observed in the context of cyclization/hydrositylation.

引用

页码：905 / 913

页数：9

共 49 条

[1] Bogdanovic B., 1979, Adv. Organomet. Chem., V17, P105
[2] Bray KL, 2001, CHEM-EUR J, V7, P4205, DOI 10.1002/1521-3765(20011001)7:19<4205::AID-CHEM4205>3.0.CO
[3] 2-Q
[4] Halide redistribution in Pd-catalysed 1,6-diene cycloisomerisation
Bray, KL
Fairlamb, IJS
Lloyd-Jones, GC
[J]. CHEMICAL COMMUNICATIONS, 2001, (02) : 187 - 188
[5] PALLADIUM(II) CATALYSTS FOR LIVING ALTERNATING COPOLYMERIZATION OF OLEFINS AND CARBON-MONOXIDE
BROOKHART, M
RIX, FC
DESIMONE, JM
BARBORAK, JC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (14) : 5894 - 5895
[6] Mechanistic studies of catalytic olefin dimerization reactions using electrophilic eta(3)-allyl-palladium(II) complexes
DiRenzo, GM
White, PS
Brookhart, M
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (26) : 6225 - 6234
[7] Mechanistic studies of the cycloisomerization of dimethyl diallylmalonate catalyzed by a cationic palladium phenanthroline complex
Goj, LA
Widenhoefer, RA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (45) : 11133 - 11147
[8] GOJ LA, UNPUB
[9] PALLADIUM-CATALYZED AND RHODIUM-CATALYZED CYCLIZATION OF 1,6-DIENES, 1,7-DIENES AND 1,8-DIENES TO CYCLOPENTENES AND METHYLENECYCLOPENTENES - CRYSTAL-STRUCTURE OF DICHLORO(4,4-DIACETYLHEPTA-1,6-DIENE)PLATINUM(II)
GRIGG, R
MALONE, JF
MITCHELL, TRB
RAMASUBBU, A
SCOTT, RM
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (08): : 1745 - 1754
[10] RING-CLOSING METATHESIS AND RELATED PROCESSES IN ORGANIC-SYNTHESIS
GRUBBS, RH
MILLER, SJ
FU, GC
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1995, 28 (11) : 446 - 452

← 1 2 3 4 5 →