Homogeneous catalytic hydroamination of alkynes and allenes with ammonia

被引：319

作者：

Lavallo, Vincent ^{[1
]}

Frey, Guido D. ^{[1
]}

Donnadieu, Bruno ^{[1
]}

Soleilhavoup, Michele ^{[1
]}

Bertrand, Guy ^{[1
]}

机构：

[1] Univ Calif Riverside, Dept Chem, UCR CNRS Joint Res Chem Lab UMI 2957, Riverside, CA 92521 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2008年 / 47卷 / 28期

关键词：

alkynes; ammonia; gold; hydroamination; nitrogen heterocycles;

D O I：

10.1002/anie.200801136

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) A golden ticket to the synthesis of reactive nitrogen-containing compounds, such as imines, enamines, and allyl amines, through the addition of NH3 to unsaturated bonds is the cationic cyclic (alkyl)-(amino)carbene-gold(I) catalyst shown in blue (Dipp=diisopropylphenyl). An ideal initial step for the preparation of simple bulk chemicals, this reaction is also useful for the synthesis of more complex molecules (see examples). © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：5224 / 5228

页数：5

共 93 条

[1] A highly reactive titanium precatalyst for intramolecular hydroamination reactions [J].

Ackermann, L ;

Bergman, RG .

ORGANIC LETTERS, 2002, 4 (09) :1475-1478

[2] Asymmetric hydroamination of non-activated carbon-carbon multiple bonds [J].

Aillaud, Isabelle ;

Collin, Jacqueline ;

Hannedouche, Jerome ;

Schulz, Emmanuelle .

DALTON TRANSACTIONS, 2007, (44) :5105-5118

[3] Transition-metal-catalyzed addition of heteroatom-hydrogen bonds to alkynes [J].

Alonso, F ;

Beletskaya, IP ;

Yus, M .

CHEMICAL REVIEWS, 2004, 104 (06) :3079-3159

[4] Proton-catalyzed hydroamination and hydroarylation reactions of anilines and alkenes: A dramatic effect of counteranions on reaction efficiency [J].

Anderson, LL ;

Arnold, J ;

Bergman, RG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (42) :14542-14543

[5] Recent advances in organothorium and organouranium catalysis [J].

Andrea, Tamer ;

Eisen, Moris S. .

CHEMICAL SOCIETY REVIEWS, 2008, 37 (03) :550-567

[6] Organoactinides in catalysis [J].

Barnea, Eyal ;

Eisen, Moris S. .

COORDINATION CHEMISTRY REVIEWS, 2006, 250 (7-8) :855-899

[7] Catalytic Markovnikov and anti-Markovnikov functionalization of alkenes and alkynes: Recent developments and trends [J].

Beller, M ;

Seayad, J ;

Tillack, A ;

Jiao, H .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (26) :3368-3398

[8]

Beller M., 2004, ANGEW CHEM, V116, P3448

[9] Hydrogen addition to the Andrussow process for HCN synthesis [J].

Bodke, AS ;

Olschki, DA ;

Schmidt, LD .

APPLIED CATALYSIS A-GENERAL, 2000, 201 (01) :13-22

[10] 1,1,2,2,2,2,3,3,3,3-DECACARBONYL-1-(ETA-CYCLOHEXA-1,3-DIENE)-TRIANGULO-TRIOSMIUM - NOVEL INTERMEDIATE IN SYNTHETIC OSMIUM CLUSTER CHEMISTRY [J].

BRYAN, EG ;

JOHNSON, BFG ;

LEWIS, J .

JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1977, (14) :1328-1330

← 1 2 3 4 5 6 7 8 9 10 →