Catalytic activation of C-H and C-C bonds of allylamines via olefin isomerization by transition metal complexes

被引：46

作者：

Jun, CH ^{[1
]}

Lee, H ^{[1
]}

Park, JB ^{[1
]}

Lee, DY ^{[1
]}

机构：

[1] Yonsei Univ, Dept Chem, Seoul 120749, South Korea

来源：

ORGANIC LETTERS | 1999年 / 1卷 / 13期

关键词：

D O I：

10.1021/ol990357b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The metal-catalyzed reaction of olefins with allylamines bearing coordination sites (2-pyridyl groups) was studied. With Ru-3(CO)(12) as catalyst, activation of C-H bonds led to the formation of ketimines that were hydrolyzed to give asymmetric ketones. With [(C8H14)(2)RhCl](2), both C-H and C-C bonds were activated and symmetric ketones were formed on hydrolysis. The reaction involves double bond migration of the allylamine to form an aldimine.

引用

收藏

页码：2161 / 2164

页数：4

相关论文

共 38 条

[1] Ru3(CO)12- and Rh4(CO)12-catalyzed reactions of pyridylolefins or N-(2-pyridyl)enamines with CO and olefins.: Carbonylation at olefinic C-H bonds [J].

Chatani, N ;

Ishii, Y ;

Ie, Y ;

Kakiuchi, F ;

Murai, S .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (15) :5129-5136

[2]

Dyker G, 1999, ANGEW CHEM INT EDIT, V38, P1699, DOI 10.1002/(SICI)1521-3773(19990614)38:12<1698::AID-ANIE1698>3.0.CO

[3]

2-6

[4] Ru3(CO)12-catalyzed site-selective carbonylation reactions at a C-H bond in aza-heterocycles [J].

Fukuyama, T ;

Chatani, N ;

Tatsumi, J ;

Kakiuchi, F ;

Murai, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (44) :11522-11523

[5] Synthesis of doubly unsaturated aldehydes and ketones by a novel beta-decarbopalladation [J].

Harayama, H ;

Kuroki, T ;

Kimura, M ;

Tanaka, S ;

Tamaru, Y .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (21) :2352-2354

[6] MECHANISM OF THE ASYMMETRIC ISOMERIZATION OF ALLYLAMINES TO ENAMINES CATALYZED BY 2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL RHODIUM COMPLEXES [J].

INOUE, S ;

TAKAYA, H ;

TANI, K ;

OTSUKA, S ;

SATO, T ;

NOYORI, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (12) :4897-4905

[7]

JARDINE FH, 1987, CHEM METAL CARBON BO, P736

[8] Chelation-assisted alkylation of benzylamine derivatives by Ru0 catalyst [J].

Jun, CH ;

Hwang, DC ;

Na, SJ .

CHEMICAL COMMUNICATIONS, 1998, (13) :1405-1406

[9] Chelation-assisted intermolecular hydroacylation: Direct synthesis of ketone from aldehyde and 1-alkene [J].

Jun, CH ;

Lee, H ;

Hong, JB .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (05) :1200-1201

[10]

Jun CH, 1999, SYNLETT, P1

← 1 2 3 4 →