SYNTHESIS OF ARYL-SUBSTITUTED ALLYLIC AMINES VIA PALLADIUM-CATALYZED COUPLING OF ARYL IODIDES, NONCONJUGATED DIENES, AND AMINES

被引：55

作者：

LAROCK, RC

WANG, Y

LU, YD

RUSSELL, CE

机构：

[1] Department of Chemistry, Iowa State University, Ames

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 26期

关键词：

D O I：

10.1021/jo00105a030

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The palladium-catalyzed coupling of aryl iodides, nonconjugated dienes, and primary and secondary amines provides omega-aryl allylic amines in good yields by a process involving arylpalladium formation and addition to the less-substituted C-C double bond of the diene, palladium migration to form a pi-allylpalladium intermediate, and nucleophilic displacement of palladium by the amine.

引用

收藏

页码：8107 / 8114

页数：8

相关论文

共 14 条

[1]

AKERMARK B, 1975, TETRAHEDRON LETT, P3733

[2] PALLADIUM-CATALYZED ARYLATION AND VINYLATION OF 1,4-DIENES [J].

BENDER, DD ;

STAKEM, FG ;

HECK, RF .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (07) :1278-1284

[3]

GODLESKI SA, 1991, COMPREHENSIVE ORGANI

[4] A PALLADIUM-MEDIATED APPROACH TO CONSTRUCTION OF NITROGEN-HETEROCYCLES [J].

HARRIS, GD ;

HERR, RJ ;

WEINREB, SM .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (09) :2528-2530

[5]

HECK RF, 1982, ORG REACTIONS, V27, P345

[6]

HECK RF, 1985, PALLADIUM REAGENTS O, pCH6

[7]

HECK RF, 1991, COMPREHENSIVE ORGANI

[8] PALLADIUM-CATALYZED CROSS-COUPLING OF ARYL HALIDES AND OLEFINIC EPOXIDES VIA PALLADIUM MIGRATION [J].

LAROCK, RC ;

LEUNG, WY .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (26) :6244-6245

[9] SYNTHESIS, STEREOCHEMISTRY, MECHANISMS OF FORMATION, AND X-RAY CRYSTAL-STRUCTURES OF ENANTIOMERICALLY PURE PI-ALLYLPALLADIUM COMPOUNDS FORMED VIA PALLADIUM-PROMOTED RING-OPENING OF BICYCLIC ALKENES [J].

LAROCK, RC ;

SONG, H ;

KIM, S ;

JACOBSON, RA .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (11) :834-836

[10] PALLADIUM-CATALYZED COUPLING OF ARYL IODIDES, NONCONJUGATED DIENES, AND CARBON NUCLEOPHILES BY PALLADIUM MIGRATION [J].

LAROCK, RC ;

LU, YD ;

BAIN, AC ;

RUSSELL, CE .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (15) :4589-4590