[2.2]Paracyclophane derived bisphosphines for the activation of hydrogen by FLPs: application in domino hydrosilylation/hydrogenation of enones

被引：52

作者：

Greb, Lutz ^{[1
]}

Ona-Burgos, Pascual ^{[2
]}

Kubas, Adam ^{[3
]}

Falk, Florian C. ^{[1
]}

Breher, Frank ^{[2
]}

Fink, Karin ^{[3
]}

Paradies, Jan ^{[1
]}

机构：

[1] Karlsruhe Inst Technol, Inst Organ Chem, D-76131 Karlsruhe, Germany

[2] Karlsruhe Inst Technol, Inst Inorgan Chem, D-76131 Karlsruhe, Germany

[3] Karlsruhe Inst Technol, Inst Nanotechnol, D-76344 Eggenstein Leopoldshafen, Germany

来源：

DALTON TRANSACTIONS | 2012年 / 41卷 / 30期

关键词：

FRUSTRATED LEWIS PAIRS; CATALYZED TRANSFER HYDROGENATION; ALPHA-IMINO ESTERS; ORGANOCATALYTIC TRANSFER HYDROGENATION; HETEROLYTIC DIHYDROGEN ACTIVATION; ASYMMETRIC TRANSFER HYDROGENATION; DIRECT REDUCTIVE AMINATION; AUXILIARY BASIS-SETS; METAL-FREE; HYDROSILATION;

D O I：

10.1039/c2dt30374d

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The heterolytic splitting of hydrogen by two types of [2.2]paracyclophane derived bisphosphines (1, 2a and 2b) in combination with tris(pentafluorophenyl) borane (3) at room temperature is described. The corresponding frustrated Lewis pairs (FLPs) exhibit different behavior in the activation of hydrogen. This results from diverse steric and electronic properties of the bisphosphines. The reactivity of the frustrated Lewis pairs was exploited in the first diastereoselective domino hydrosilylation/hydrogenation reaction catalyzed by FLPs.

引用

页码：9056 / 9060

页数：5

共 70 条

[1]

Almena J., 2006, ANGEW CHEM INT EDIT, V45, P154

[2] DENSITY-FUNCTIONAL EXCHANGE-ENERGY APPROXIMATION WITH CORRECT ASYMPTOTIC-BEHAVIOR [J].

BECKE, AD .

PHYSICAL REVIEW A, 1988, 38 (06) :3098-3100

[3] B(C6F5)3 catalyzed hydrosilation of enones and silyl enol ethers [J].

Blackwell, JM ;

Morrison, DJ ;

Piers, WE .

TETRAHEDRON, 2002, 58 (41) :8247-8254

[4] The scope and limitations of intramolecular radical cyclizations of acylsilanes with alkyl, aryl, and vinyl radicals [J].

Chang, SY ;

Jiaang, WT ;

Cherng, CD ;

Tang, KH ;

Huang, CH ;

Tsai, YM .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (26) :9089-9098

[5] Metal-free catalytic hydrogenation (vol 46, pg 8050, 2007) [J].

Chase, P. A. ;

Welch, G. C. ;

Jurca, T. ;

Stephan, D. W. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (48) :9136-9136

[6] Lewis acid-catalyzed hydrogenation:: B(C6F5)3-mediated reduction of imines and nitriles with H2 [J].

Chase, Preston A. ;

Jurca, Titel ;

Stephan, Douglas W. .

CHEMICAL COMMUNICATIONS, 2008, (14) :1701-1703

[7] Metal-free catalytic hydrogenation [J].

Chase, Preston A. ;

Welch, Gregory C. ;

Jurca, Titel ;

Stephan, Douglas W. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (42) :8050-8053

[8] New paracyclophane phosphine for highly enantioselective ruthenium-catalyzed hydrogenation of prochiral ketones [J].

Cheemala, Murthy N. ;

Gayral, Maud ;

Brown, John M. ;

Rossen, Kai ;

Knochel, Paul .

SYNTHESIS-STUTTGART, 2007, (24) :3877-3885

[9] Metal-free catalytic hydrogenation of imines with tris(perfluorophenyl) borane [J].

Chen, Dianjun ;

Klankermayer, Juergen .

CHEMICAL COMMUNICATIONS, 2008, (18) :2130-2131

[10] Enantioselective Hydrogenation with Chiral Frustrated Lewis Pairs [J].

Chen, Dianjun ;

Wang, Yutian ;

Klankermayer, Juergen .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (49) :9475-9478

← 1 2 3 4 5 6 7 →