Hydrogenation of carboxylic esters catalyzed by manganese catalysts supported by bidentate NHC-phosphine ligands

被引：1

作者：

Azouzi, Karim ^{[1
]}

Pointis, Romane ^{[1
]}

Buhaibeh, Ruqaya ^{[1
]}

Fernandez, Pablo Hermosilla ^{[1
,2
]}

Pedussaut, Lucie ^{[1
]}

Boundor, Mohamed ^{[1
]}

Bonfiglio, Anna ^{[1
]}

Bruneau-Voisine, Antoine ^{[1
]}

Wei, Duo ^{[1
]}

Roisnel, Thierry

Duhayon, Carine ^{[1
]}

Casado, Miguel Angel ^{[2
]}

Valyaev, Dmitry A. ^{[1
]}

Canac, Yves ^{[1
]}

Bastin, Stephanie ^{[1
]}

Raynaud, Christophe ^{[4
]}

Sortais, Jean -Baptiste ^{[1
,3
,5
]}

机构：

[1] Univ Toulouse, LCC, CNRS, UPS, 205 route Narbonne, F-31077 Toulouse 4, France

[2] Univ Zaragoza, Dept Quim Inorgan, Inst Sintesis Quim & Catalisis Homogenea ISQCH, CSIC, C Pedro Cerbuna 12, Zaragoza 50009, Spain

[3] CNRS, ISCR, UMR6226, F-35000 Rennes, France

[4] Univ Montpellier, ICGM, CNRS, ENSCM, F-34090 Montpellier, France

[5] Inst Univ France, 1 Rue Descartes, F-75231 Paris 5, France

来源：

JOURNAL OF CATALYSIS | 2024年 / 430卷

关键词：

Manganese; Hydrogenation; Carboxylic esters; N -heterocyclic carbene; Phosphine; Earth abundant transition metals; CARBON-DIOXIDE HYDROGENATION; SELECTIVE HYDROGENATION; COMPLEXES; NITRILES; AMINES; KETONES; H-2;

D O I：

10.1016/j.jcat.2024.115334

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

A series of bidentate manganese complexes with a general structure [(kappa C-2,P-R2PCH2CH2-NHC)Mn(CO)(3)Br] (NHC = N-substituted imidazolylidene) was prepared and fully characterized. These complexes were proven to be efficient catalysts for the hydrogenation of carboxylic ester derivatives with a low catalyst loading (0.5 mol%) in 2-Me-THF at 100 degrees C in the presence of KHBEt3. The generality of this hydrogenation was exemplified with more than 25 substrates. Experimental and computational investigations allowed to propose a rational mechanism involving an anionic tricarbonyl manganese hydride complex as the active species.

引用

页数：10

共 50 条

[1] Phosphine-Imidazolyl Ligands for the Efficient Ruthenium-Catalyzed Hydrogenation of Carboxylic Esters
Junge, Kathrin
Wendt, Bianca
Westerhaus, Felix Alexander
Spannenberg, Anke
Jiao, Haijun
Beller, Matthias
CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (29) : 9011 - 9018
[2] Asymmetric Hydrogenation of Imines Using NHC-Phosphine Iridium Complexes
He, Lei
Peters, Bram B. C.
Quan, Xu
Zhao, Shaohu
Huang, Tianrui
Ren, Shuting
Andersson, Pher G.
Zhou, Taigang
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 12 (06)
[3] Fine-tuning NHC ligands for ruthenium-catalyzed hydrogenation of carboxylic esters to alcohols
Kadyrov, Renat
JOURNAL OF CATALYSIS, 2023, 426 : 173 - 177
[4] Manganese-Mediated Synthesis of NHC-Phosphine Ligand Precursors
Willot, Jeremy
Fatima, Sana
Duhayon, Carine
Lugan, Noel
Canac, Yves
Valyaev, Dmitry A.
HELVETICA CHIMICA ACTA, 2024, 107 (04)
[5] Cationic NHC-Phosphine Iridium Complexes: Highly Active Catalysts for Base-Free Hydrogenation of Ketones
Quan, Xu
Kerdphon, Sutthichat
Peters, Bram B. C.
Rujirawanich, Janjira
Krajangsri, Suppachai
Jongcharoenkamol, Jira
Andersson, Pher G.
CHEMISTRY-A EUROPEAN JOURNAL, 2020, 26 (58) : 13311 - 13316
[6] Hydrogenation of Carboxylic Esters Catalyzed by Phosphine-Free Bis-N-heterocyclic Carbene Manganese Complexes
Azouzi, Karim
Pedussaut, Lucie
Pointis, Romane
Bonfiglio, Anna
Riddhi, Riddhi Kumari
Duhayon, Carine
Bastin, Stephanie
Sortais, Jean-Baptiste
ORGANOMETALLICS, 2023, 42 (14) : 1832 - 1838
[7] Ruthenium catalyzed asymmetric transfer hydrogenation employing novel bidentate abnormal NHC ligands
Tinnis, Fredrik
Adolfsson, Hans
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2011, 242
[8] Hydrogenation of Alkenes Catalyzed by Mn(I) Alkyl Complexes Bearing NHC Phosphine Ligands
Zobernig, Daniel P.
Stöger, Berthold
Veiros, Luis F.
Kirchner, Karl
ChemCatChem, 2024, 16 (22)
[9] Hydrogenation of Esters by Manganese Catalysts
Li, Xiao-Gen
Li, Fu
Xu, Yue
Xiao, Li-Jun
Xie, Jian-Hua
Zhou, Qi-Lin
ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (04) : 744 - 749
[10] Hydrogenation of Carbonyl Derivatives Catalysed by Manganese Complexes Bearing Bidentate Pyridinyl-Phosphine Ligands
Wei, Duo
Bruneau-Voisine, Antoine
Chauvin, Teo
Dorcet, Vincent
Roisnel, Thierry
Valyaev, Dmitry A.
Lugan, Noel
Sortais, Jean-Baptiste
ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (04) : 676 - 681

← 1 2 3 4 5 →