Asymmetric catalytic hydroamination of activated olefins in ionic liquids

被引：32

作者：

Fadini, Luca ^{[1
]}

Togni, Antonio

机构：

[1] Univ Nacl Columbia, Dept Quim, Sede De Bogota, Israel

[2] ETH Honggerberg, Dept chem & Appl Biosci, CH-8093 Zurich, Switzerland

来源：

HELVETICA CHIMICA ACTA | 2007年 / 90卷 / 02期

关键词：

D O I：

10.1002/hlca.200790048

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The addition of a series of both aliphatic and aromatic amines to electron-poor olefins was investigated using [Ni(Pigiphos)(THF)](2+) as catalyst (with different counterions) in various ionic liquids based on imidazolium- and picolinium-salt derivatives. The catalysts gave rise to selectivities comparable to those obtained when the reaction was conducted in neat organic solvents (ee up to 66%), but significant higher activities, with a total turnover number (TON) of up to 300.

引用

页码：411 / 424

页数：14

共 45 条

[1] Iridium(I)-catalyzed asymmetric intermolecular hydroarylation of norbornene with benzamide [J].

Aufdenblatten, R ;

Diezi, S ;

Togni, A .

MONATSHEFTE FUR CHEMIE, 2000, 131 (12) :1345-1350

[2] Novel hydroamination reactions in a liquid-liquid two-phase catalytic system [J].

Bódis, J ;

Müller, TE ;

Lercher, JA .

GREEN CHEMISTRY, 2003, 5 (02) :227-231

[3] Intermolecular highly regioselective hydroamination of alkenes with ligandless Platinum(II) catalysts in ionic solvents:: Activation role of n-Bu4PBr [J].

Brunet, JJ ;

Chu, NC ;

Diallo, O .

ORGANOMETALLICS, 2005, 24 (13) :3104-3110

[4] Platinum-catalyzed intermolecular hydroamination of terminal alkynes [J].

Brunet, JJ ;

Chu, NC ;

Diallo, O ;

Vincendeau, S .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2005, 240 (1-2) :245-248

[5] Catalytic intennolecular hydroamination of alkenes - Beneficial effect of ionic solvents [J].

Brunet, JJ ;

Chu, NC ;

Diallo, O ;

Mothes, E .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2003, 198 (1-2) :107-110

[6]

Choong E.S., 2005, B KOREAN CHEM SOC, V26, P1321

[7] Homogeneous catalysis - new approaches to catalyst separation, recovery, and recycling [J].

Cole-Hamilton, DJ .

SCIENCE, 2003, 299 (5613) :1702-1706

[8] Lanthanide complexes coordinated by N-substituted (R)-1,1′-binaphthyl-2,2′-diamido ligands in the catalysis of enantioselective intramolecular hydroamination [J].

Collin, J ;

Daran, JC ;

Jacquet, O ;

Schulz, E ;

Trifonov, A .

CHEMISTRY-A EUROPEAN JOURNAL, 2005, 11 (11) :3455-3462

[9] The [IrCl(diphosphine)](2)/fluoride system. Developing catalytic asymmetric olefin hydroamination [J].

Dorta, R ;

Egli, P ;

Zurcher, F ;

Togni, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (44) :10857-10858

[10] Ionic liquid (molten salt) phase organometallic catalysis [J].

Dupont, J ;

de Souza, RF ;

Suarez, PAZ .

CHEMICAL REVIEWS, 2002, 102 (10) :3667-3691

← 1 2 3 4 5 →