Nickel(II)-catalyzed highly enantioselective hydrophosphination of methacrylonitrile

被引：155

作者：

Sadow, AD ^{[1
]}

Haller, I ^{[1
]}

Fadini, L ^{[1
]}

Togni, A ^{[1
]}

机构：

[1] ETH Honggerberg, Swiss Fed Inst Technol, Dept Chem & Appl Biosci, CH-8093 Zurich, Switzerland

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2004年 / 126卷 / 45期

关键词：

D O I：

10.1021/ja0449574

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The dicationic Ni(II) complex [Ni(Pigiphos)(THF)](ClO4)2, [1](ClO4)2 ((R)-(S)-Pigiphos = bis-{(R)-1-[(S)-2-(diphenylphosphino)ferrocenyl]ethyl}cyclohexylphosphine), catalyzes the addition of bulky aliphatic secondary phosphines to methaacrylonitrile. This hydrophosphination reaction reaches TON = 900 and enantioselectivities up to 94%. A catalytic cycle involving 1,4-conjugate addition of R2PH to methacrylonitrile is supported by the isolation and characterization of a catalytically active N-coordinated, methacrylonitrile Ni complex. Copyright © 2004 American Chemical Society.

引用

页码：14704 / 14705

页数：2

共 22 条

[1] Synthesis and characterization of chiral bis-ferrocenyl triphosphine Ni(II) and Rh(III) complexes and their use as catalyst precursors for acetalization reactions [J].

Barbaro, P ;

Bianchini, C ;

Oberhauser, W ;

Togni, A .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1999, 145 (1-2) :139-146

[2] A NEW CHIRAL TRIDENTATE FERROCENYL LIGAND - SYNTHESIS AND CHARACTERIZATION OF ITS PALLADIUM(II) AND NICKEL(II) COMPLEXES [J].

BARBARO, P ;

TOGNI, A .

ORGANOMETALLICS, 1995, 14 (07) :3570-3573

[3] t-BuOK-mediated hydrophosphination of functionalized alkenes:: a novel synthesis of chiral P,N- and P,P-ligands [J].

Bunlaksananusorn, T ;

Knochel, P .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (14) :4595-4601

[4] Chemoselective platinum(0)-catalysed hydrophosphination of ethyl acrylate [J].

Costa, E ;

Pringle, PG ;

Worboys, K .

CHEMICAL COMMUNICATIONS, 1998, (01) :49-50

[5] Widening the roof: Synthesis and characterization of new chiral C1-symmetric octahydrofluorenyl organolanthanide catalysts and their implementation in the stereoselective cyclizations of aminoalkenes and phosphinoalkenes [J].

Douglass, Michael R. ;

Ogasawara, Masamichi ;

Hong, Sukwon ;

Metz, Matthew V. ;

Marks, Tobin J. .

Organometallics, 2002, 21 (02) :283-292

[6] Organolanthanide-catalyzed intramolecular hydrophosphination/cyclization of phosphinoalkenes and phosphinoalkynes [J].

Douglass, MR ;

Marks, TJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (08) :1824-1825

[7] Ni(II) complexes containing chiral tridentate phosphines as new catalysts for the hydroamination of activated olefins [J].

Fadini, L ;

Togni, A .

CHEMICAL COMMUNICATIONS, 2003, (01) :30-31

[8]

FADINI L, 2004, CHIMIA, P54

[9]

Hintermann L, 2003, EUR J INORG CHEM, P601

[10] ACID-CATALYZED ADDITION OF PHOSPHINE TO OLEFINS [J].

HOFF, MC ;

HILL, P .

JOURNAL OF ORGANIC CHEMISTRY, 1959, 24 (03) :356-359

← 1 2 3 →