Intramolecular frustrated N/B lewis pairs by enamine hydroboration

被引：132

作者：

Schwendemann, Sina ^{[1
]}

Froehlich, Roland ^{[1
]}

Kehr, Gerald ^{[1
]}

Erker, Gerhard ^{[1
]}

机构：

[1] Univ Munster, Inst Organ Chem, D-48149 Munster, Germany

来源：

CHEMICAL SCIENCE | 2011年 / 2卷 / 09期

关键词：

FREE CATALYTIC-HYDROGENATION; HETEROLYTIC DIHYDROGEN ACTIVATION; METAL-FREE; ADDITION-REACTIONS; BOND ACTIVATION; ACID; REACTIVITY; H-2; MECHANISM; IMINES;

D O I：

10.1039/c1sc00124h

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A series of enamines undergoes anti-Markovnikov hydroboration with Piers' borane HB(C6F5)(2) to yield C-2-bridged frustrated N/B Lewis pairs, featuring weak N center dot center dot center dot B interaction. Some examples show typical frustrated Lewis pair reactions with dihydrogen or with 1-alkynes. One such N/B FLP serves as an active catalyst for the hydrogenation of enamines. Many of the new compounds were characterized by X-ray diffraction.

引用

页码：1842 / 1849

页数：8

共 97 条

[11] Hydrogen and amine activation by a frustrated Lewis pair of a bulky n-heterocyclic carbene and B(C6F5)3 [J].

Chase, Preston A. ;

Stephan, Douglas W. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (39) :7433-7437

[12] 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

[13] 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

[14] Frustrated Lewis pairs derived from N-heterocyclic carbenes and Lewis acids [J].

Chase, Preston A. ;

Gille, Austin L. ;

Gilbert, Thomas M. ;

Stephan, Douglas W. .

DALTON TRANSACTIONS, 2009, (35) :7179-7188

[15] Carbon-Carbon Bond Activation by 1,1-Carboboration of Internal Alkynes [J].

Chen, Chao ;

Kehr, Gerald ;

Froehlich, Roland ;

Erker, Gerhard .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (39) :13594-13595

[16] Exploring the Limits of Frustrated Lewis Pair Chemistry with Alkynes: Detection of a System that Favors 1,1-Carboboration over Cooperative 1,2-P/B-Addition [J].

Chen, Chao ;

Eweiner, Florian ;

Wibbeling, Birgit ;

Froehlich, Roland ;

Senda, Shunsuke ;

Ohki, Yasuhiro ;

Tatsumi, Kazuyuki ;

Grimme, Stefan ;

Kehr, Gerald ;

Erker, Gerhard .

CHEMISTRY-AN ASIAN JOURNAL, 2010, 5 (10) :2199-2208

[17] Remarkably variable reaction modes of frustrated Lewis pairs with non-conjugated terminal diacetylenes [J].

Chen, Chao ;

Froehlich, Roland ;

Kehr, Gerald ;

Erker, Gerhard .

CHEMICAL COMMUNICATIONS, 2010, 46 (20) :3580-3582

[18]

Chen D., 2010, Angewandte Chemie, V122, P9665

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

Chen, Dianjun ;

Klankermayer, Juergen .

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

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

Chen, Dianjun ;

Wang, Yutian ;

Klankermayer, Juergen .

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

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