New C-N and C-C bond forming reactions catalyzed by titanium complexes

被引：294

作者：

Odom, AL ^{[1
]}

机构：

[1] Michigan State Univ, Dept Chem, E Lansing, MI 48911 USA

来源：

DALTON TRANSACTIONS | 2005年 / 02期

关键词：

D O I：

10.1039/b415701j

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Titanium(IV) complexes with two basic dimethylamido ligands can be efficient catalysts for alkyne hydroamination by primary amines. Readily prepared pyrrolyl ligands have proven to be especially useful in generating active catalysts for hydroamination and hydrohydrazination. From these reactions, new methodologies for the synthesis of imines, hydrazones, alpha,beta-unsaturated imines, pyridines, indoles, and pyrroles have developed. In addition, a new reaction that is mechanistically related to hydroamination, alkyne iminoamination, has been discovered. Iminoamination, which is a multicomponent coupling between an amine, alkyne, and isonitrile, provides unsymmetrical alpha,beta-unsaturated beta-iminoamines in a single, titanium-catalyzed step.

引用

页码：225 / 233

页数：9

共 101 条

[1] TiCl4-catalyzed intermolecular hydroamination reactions of norbornene [J].

Ackermann, L ;

Kaspar, LT ;

Gschrei, CJ .

ORGANIC LETTERS, 2004, 6 (15) :2515-2518

[2] Use of group 4 bis(sulfonamido) complexes in the intramolecular hydroamination of alkynes and allenes [J].

Ackermann, L ;

Bergman, RG ;

Loy, RN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (39) :11956-11963

[3] TiCl4-catalyzed intermolecular hydroamination reactions [J].

Ackermann, L .

ORGANOMETALLICS, 2003, 22 (22) :4367-4368

[4] Catalytic hydroamination of alkynes and norbornene with neutral and cationic tantalum imido complexes [J].

Anderson, LL ;

Arnold, J ;

Bergman, RG .

ORGANIC LETTERS, 2004, 6 (15) :2519-2522

[5] Organolanthanide-catalyzed hydroamination/cyclization. Efficient allene-based transformations for the syntheses of naturally occurring alkaloids [J].

Arredondo, VM ;

Tian, S ;

McDonald, FE ;

Marks, TJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (15) :3633-3639

[6] VARIABLE REGIOCHEMISTRY IN THE STOICHIOMETRIC AND CATALYTIC HYDROAMINATION OF ALKYNES BY IMIDOZIRCONIUM COMPLEXES CAUSED BY AN UNUSUAL DEPENDENCE OF THE RATE LAW ON ALKYNE STRUCTURE AND TEMPERATURE [J].

BARANGER, AM ;

WALSH, PJ ;

BERGMAN, RG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (07) :2753-2763

[7] Rhodium(I)-catalysed hydrocarbonylation and silylcarbonylation reactions of alkynes in the presence of primary amines leading to 2-pyrrolidinones and 4-silylated 1-aza-1,3-butadienes [J].

Bärfacker, L ;

Hollmann, C ;

Eilbracht, P .

TETRAHEDRON, 1998, 54 (18) :4493-4506

[8] SYNTHESIS OF 1-AZA-1,3-DIENES AND 2-MORPHOLINO-1,3-DIENES VIA CATALYTIC AMINOMERCURIATION OF ALK-3-EN-1-YNES [J].

BARLUENGA, J ;

AZNAR, F ;

LIZ, R ;

CABAL, MP .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (20) :1375-1376

[9] CATALYTIC AMINOMERCURATION REACTIONS OF 3-ALKEN-1-YNES - AN IMPROVED METHOD FOR THE SYNTHESIS OF 2-AMINO-1,3-BUTADIENES AND 1-AZA-1,3-BUTADIENES [J].

BARLUENGA, J ;

AZNAR, F ;

VALDES, C ;

CABAL, MP .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (21) :6166-6171

[10] First [4+2] cycloaddition of alkynyl Fischer carbene complexes with heterodienes. Facile synthesis of 1,4-dihydropyridines from 1-azadienes [J].

Barluenga, J ;

Tomas, M ;

LopezPelegrin, JA ;

Rubio, E .

TETRAHEDRON LETTERS, 1997, 38 (22) :3981-3984

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