Manganese(I)-Catalyzed Enantioselective Hydrogenation of Ketones Using a Defined Chiral PNP Pincer Ligand

被引：177

作者：

Garbe, Marcel ^{[1
]}

Junge, Kathrin ^{[1
]}

Walker, Svenja ^{[1
]}

Wei, Zhihong ^{[1
]}

Jiao, Haijun ^{[1
]}

Spannenberg, Anke ^{[1
]}

Bachmann, Stephan ^{[2
]}

Scalone, Michelangelo ^{[2
]}

Beller, Matthias ^{[1
]}

机构：

[1] Univ Rostock, Leibniz Inst Katalyse eV, Albert Einstein Str 29a, D-18059 Rostock, Germany

[2] F Hoffmann La Roche Ltd, Proc Chem & Catalysis, CH-4070 Basel, Switzerland

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2017年 / 56卷 / 37期

关键词：

asymmetric hydrogenation; chiral alcohols; chiral pincer ligands; ketones; manganese; ASYMMETRIC TRANSFER HYDROGENATION; C BOND FORMATION; P-N-P'; IRON(II) COMPLEXES; CATALYTIC-HYDROGENATION; EFFICIENT; ALCOHOLS; AMINES; ALKYLATION; REDUCTION;

D O I：

10.1002/anie.201705471

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A new chiral manganese PNP pincer complex is described. The asymmetric hydrogenation of several prochiral ketones with molecular hydrogen in the presence of this complex proceeds under mild conditions (30-40 degrees C, 4 h, 30 bar H-2). Besides high catalytic activity for aromatic substrates, aliphatic ketones are hydrogenated with remarkable selectivity (e.r. up to 92:8). DFT calculations support an outer sphere hydrogenation mechanism as well as the experimentally determined stereochemistry.

引用

页码：11237 / 11241

页数：5

共 50 条

[31] Isomerization of Allylic Alcohols to Ketones Catalyzed by Well-Defined Iron PNP Pincer Catalysts
Xia, Tian
Wei, Zhihong
Spiegelberg, Brian
Jiao, Haijun
Hinze, Sandra
de Vries, Johannes G.
CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (16) : 4043 - 4049
[32] N, N-Mn(I)-catalyzed transfer hydrogenation of ketones
Luo, Renshi
Tong, Jinghui
Liu, Liang
Ouyang, Lu
Liao, Jianhua
MOLECULAR CATALYSIS, 2025, 571
[33] Hydrogenation of Aliphatic and Aromatic Nitriles Using a Defined Ruthenium PNP Pincer Catalyst
Neumann, Jacob
Bornschein, Christoph
Jiao, Haijun
Junge, Kathrin
Beller, Matthias
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (27) : 5944 - 5948
[34] Carbon dioxide hydrogenation catalysed by well-defined Mn(I) PNP pincer hydride complexes
Bertini, Federica
Glatz, Mathias
Gorgas, Nikolaus
Stoeger, Berthold
Peruzzini, Maurizio
Veiros, Luis F.
Kirchner, Karl
Gonsalvi, Luca
CHEMICAL SCIENCE, 2017, 8 (07) : 5024 - 5029
[35] Asymmetric Transfer Hydrogenation of Diaryl Ketones with Ethanol Catalyzed by Chiral NCP Pincer Iridium Complexes
Qian, Lu
Tang, Xixia
Wang, Yulei
Liu, Guixia
Huang, Zheng
CHINESE JOURNAL OF CHEMISTRY, 2022, 40 (10) : 1131 - 1136
[36] Asymmetric Transfer Hydrogenation of Ketones with Well-Defined Manganese(I) PNN and PNNP Complexes
Demmans, Karl Z.
Olson, Maxwell E.
Morris, Robert H.
ORGANOMETALLICS, 2018, 37 (24) : 4608 - 4618
[37] Transfer hydrogenation of aldehydes and ketones catalyzed using an aminophosphinite POCNH pincer complex of Ni(II)
Segizbayev, Medet
Oztopcu, Ozgur
Hayrapetyan, Davit
Shakhman, Dinmukhamed
Lyssenko, Konstantin A.
Khalimon, Andrey Y.
DALTON TRANSACTIONS, 2020, 49 (34) : 11950 - 11957
[38] The impact of Metal-Ligand Cooperation in Hydrogenation of Carbon Dioxide Catalyzed by Ruthenium PNP Pincer
Filonenko, Georgy A.
Conley, Matthew P.
Coperet, Christophe
Lutz, Martin
Hensen, Emiel J. M.
Pidko, Evgeny A.
ACS CATALYSIS, 2013, 3 (11): : 2522 - 2526
[39] Ligand Effect in Alkali-Metal-Catalyzed Transfer Hydrogenation of Ketones
Alshakova, Iryna D.
Foy, Hayden C.
Dudding, Travis
Nikonov, Georgii I.
CHEMISTRY-A EUROPEAN JOURNAL, 2019, 25 (50) : 11734 - 11744
[40] Manganese PNP-pincer catalyzed isomerization of allylic/homo-allylic alcohols to ketones - activity, selectivity, efficiency
Xia, Tian
Spiegelberg, Brian
Wei, Zhihong
Jiao, Haijun
Tin, Sergey
Hinze, Sandra
de Vries, Johannes G.
CATALYSIS SCIENCE & TECHNOLOGY, 2019, 9 (22) : 6327 - 6334

← 1 2 3 4 5 →