Metal-Free Catalytic Hydrogenation of Polar Substrates by Frustrated Lewis Pairs

被引：264

作者：

Stephan, Douglas W. ^{[1
]}

Greenberg, Sharonna ^{[1
]}

Graham, Todd W. ^{[1
]}

Chase, Preston ^{[1
]}

Hastie, Jeff J. ^{[1
]}

Geier, Stephen J. ^{[1
]}

Farrell, Jeffrey M. ^{[1
]}

Brown, Christopher C. ^{[1
]}

Heiden, Zachariah M. ^{[1
]}

Welch, Gregory C. ^{[2
]}

Ullrich, Matthias ^{[1
]}

机构：

[1] Univ Toronto, Dept Chem, Toronto, ON M5S 3H6, Canada

[2] Univ Windsor, Dept Chem & Biochem, Windsor, ON N9B 3P4, Canada

来源：

INORGANIC CHEMISTRY | 2011年 / 50卷 / 24期

基金：

加拿大自然科学与工程研究理事会;

关键词：

ORGANOCATALYTIC TRANSFER HYDROGENATION; ENANTIOSELECTIVE HYDROGENATION; IMINES; ACTIVATION; ACID; REDUCTION; MECHANISM; DIHYDROGEN; KETONES; BORANES;

D O I：

10.1021/ic200663v

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

In 2006, our group reported the first metal-free systems that reversibly activate hydrogen. This finding was extended to the discovery of "frustrated Lewis pair" (FLP) catalysts for hydrogenation. It is this catalysis that is the focal point of this article. The development and applications of such FLP hydrogenation catalysts are reviewed, and some previously unpublished data are reported. The scope of the substrates is expanded. Optimal conditions and functional group tolerance are considered and applied to targets of potential commercial significance. Recent developments in asymmetric FLP hydrogenations are also reviewed. The future of FLP hydrogenation catalysts is considered.

引用

页码：12338 / 12348

页数：11

共 61 条

[1] Ruthenium dihydride RuH2(PPh3)2((R,R)-cyclohexyldiamine) and ruthenium monohydride RuHCl(PPh3)2((R,R)-cyclohexyldiamine):: Active catalyst and catalyst precursor for the hydrogenation of ketones and imines [J].

Abdur-Rashid, K ;

Lough, AJ ;

Morris, RH .

ORGANOMETALLICS, 2000, 19 (14) :2655-2657

[2] Organocatalytic hydride transfers: A new concept in asymmetric hydrogenations [J].

Adolfsson, H .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (22) :3340-3342

[3] Asymmetric transfer hydrogenation in aqueous media catalyzed by resin-supported peptide having a polyleucine tether [J].

Akagawa, Kengo ;

Akabane, Hajime ;

Sakamoto, Seiji ;

Kudo, Kazuaki .

TETRAHEDRON-ASYMMETRY, 2009, 20 (04) :461-466

[4] Catalytic Hydrogenation of Sensitive Organometallic Compounds by Antagonistic N/B Lewis Pair Catalyst Systems [J].

Axenov, Kirill V. ;

Kehr, Gerald ;

Froehlich, Roland ;

Erker, Gerhard .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (10) :3454-+

[5] Hydrogenation without a transition-metal catalyst:: On the mechanism of the base-catalyzed hydrogenation of ketones [J].

Berkessel, A ;

Schubert, TJS ;

Müller, TN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (29) :8693-8698

[6] Metal-free conversion of methane and cycloalkanes to amines and amides by employing a borylnitrene [J].

Bettinger, Holger F. ;

Filthaus, Matthias ;

Bornemann, Holger ;

Oppel, Iris M. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (25) :4744-4747

[7] Insertion into dihydrogen employing the nitrogen centre of a borylnitrene [J].

Bettinger, Holger F. ;

Filthaus, Matthias ;

Neuhaus, Patrik .

CHEMICAL COMMUNICATIONS, 2009, (16) :2186-2188

[8] PHOTOCHEMICAL SYNTHESIS OF 2,3-DIHYDROINDOLES FROM N-ARYL ENAMINES [J].

CHAPMAN, OL ;

EIAN, GL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (19) :5329-&

[9] 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

[10] 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

← 1 2 3 4 5 6 7 →