Robust and efficient hydrogenation of carbonyl compounds catalysed by mixed donor Mn(I) pincer complexes
Any catalyst should be efficient and stable to be implemented in practice. This requirement is particularly valid for manganese hydrogenation catalysts. While representing a more sustainable alternative to conventional noble metal-based systems, manganese hydrogenation catalysts are prone to degrade...
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| Published in: | Nature communications Vol. 12; no. 1; pp. 12 - 8 |
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| Main Authors: | , , , , , , |
| Format: | Journal Article |
| Language: | English |
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Nature Publishing Group UK
04.01.2021
Nature Publishing Group Nature Portfolio |
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| ISSN: | 2041-1723, 2041-1723 |
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| Abstract | Any catalyst should be efficient and stable to be implemented in practice. This requirement is particularly valid for manganese hydrogenation catalysts. While representing a more sustainable alternative to conventional noble metal-based systems, manganese hydrogenation catalysts are prone to degrade under catalytic conditions once operation temperatures are high. Herein, we report a highly efficient Mn(I)-CNP pre-catalyst which gives rise to the excellent productivity (TOF° up to 41 000 h
−1
) and stability (TON up to 200 000) in hydrogenation catalysis. This system enables near-quantitative hydrogenation of ketones, imines, aldehydes and formate esters at the catalyst loadings as low as 5–200 p.p.m. Our analysis points to the crucial role of the catalyst activation step for the catalytic performance and stability of the system. While conventional activation employing alkoxide bases can ultimately provide catalytically competent species under hydrogen atmosphere, activation of Mn(I) pre-catalyst with hydride donor promoters, e.g. KHBEt
3
, dramatically improves catalytic performance of the system and eliminates induction times associated with slow catalyst activation.
Manganese-based hydrogenation catalysts are sensitive to high temperatures and may degrade under industrially relevant conditions. Here, the authors report a highly efficient manganese pincer pre-catalyst displaying high TOF values (up to 41 000 h
−1
) and stability (TON up to 200 000) at loadings as low as 5-200 ppm. |
|---|---|
| AbstractList | Any catalyst should be efficient and stable to be implemented in practice. This requirement is particularly valid for manganese hydrogenation catalysts. While representing a more sustainable alternative to conventional noble metal-based systems, manganese hydrogenation catalysts are prone to degrade under catalytic conditions once operation temperatures are high. Herein, we report a highly efficient Mn(I)-CNP pre-catalyst which gives rise to the excellent productivity (TOF° up to 41 000 h
−1
) and stability (TON up to 200 000) in hydrogenation catalysis. This system enables near-quantitative hydrogenation of ketones, imines, aldehydes and formate esters at the catalyst loadings as low as 5–200 p.p.m. Our analysis points to the crucial role of the catalyst activation step for the catalytic performance and stability of the system. While conventional activation employing alkoxide bases can ultimately provide catalytically competent species under hydrogen atmosphere, activation of Mn(I) pre-catalyst with hydride donor promoters, e.g. KHBEt
3
, dramatically improves catalytic performance of the system and eliminates induction times associated with slow catalyst activation. Any catalyst should be efficient and stable to be implemented in practice. This requirement is particularly valid for manganese hydrogenation catalysts. While representing a more sustainable alternative to conventional noble metal-based systems, manganese hydrogenation catalysts are prone to degrade under catalytic conditions once operation temperatures are high. Herein, we report a highly efficient Mn(I)-CNP pre-catalyst which gives rise to the excellent productivity (TOF° up to 41 000 h −1 ) and stability (TON up to 200 000) in hydrogenation catalysis. This system enables near-quantitative hydrogenation of ketones, imines, aldehydes and formate esters at the catalyst loadings as low as 5–200 p.p.m. Our analysis points to the crucial role of the catalyst activation step for the catalytic performance and stability of the system. While conventional activation employing alkoxide bases can ultimately provide catalytically competent species under hydrogen atmosphere, activation of Mn(I) pre-catalyst with hydride donor promoters, e.g. KHBEt 3 , dramatically improves catalytic performance of the system and eliminates induction times associated with slow catalyst activation. Manganese-based hydrogenation catalysts are sensitive to high temperatures and may degrade under industrially relevant conditions. Here, the authors report a highly efficient manganese pincer pre-catalyst displaying high TOF values (up to 41 000 h −1 ) and stability (TON up to 200 000) at loadings as low as 5-200 ppm. Manganese-based hydrogenation catalysts are sensitive to high temperatures and may degrade under industrially relevant conditions. Here, the authors report a highly efficient manganese pincer pre-catalyst displaying high TOF values (up to 41 000 h−1) and stability (TON up to 200 000) at loadings as low as 5-200 ppm. Any catalyst should be efficient and stable to be implemented in practice. This requirement is particularly valid for manganese hydrogenation catalysts. While representing a more sustainable alternative to conventional noble metal-based systems, manganese hydrogenation catalysts are prone to degrade under catalytic conditions once operation temperatures are high. Herein, we report a highly efficient Mn(I)-CNP pre-catalyst which gives rise to the excellent productivity (TOF° up to 41 000 h ) and stability (TON up to 200 000) in hydrogenation catalysis. This system enables near-quantitative hydrogenation of ketones, imines, aldehydes and formate esters at the catalyst loadings as low as 5-200 p.p.m. Our analysis points to the crucial role of the catalyst activation step for the catalytic performance and stability of the system. While conventional activation employing alkoxide bases can ultimately provide catalytically competent species under hydrogen atmosphere, activation of Mn(I) pre-catalyst with hydride donor promoters, e.g. KHBEt , dramatically improves catalytic performance of the system and eliminates induction times associated with slow catalyst activation. Any catalyst should be efficient and stable to be implemented in practice. This requirement is particularly valid for manganese hydrogenation catalysts. While representing a more sustainable alternative to conventional noble metal-based systems, manganese hydrogenation catalysts are prone to degrade under catalytic conditions once operation temperatures are high. Herein, we report a highly efficient Mn(I)-CNP pre-catalyst which gives rise to the excellent productivity (TOF° up to 41 000 h−1) and stability (TON up to 200 000) in hydrogenation catalysis. This system enables near-quantitative hydrogenation of ketones, imines, aldehydes and formate esters at the catalyst loadings as low as 5–200 p.p.m. Our analysis points to the crucial role of the catalyst activation step for the catalytic performance and stability of the system. While conventional activation employing alkoxide bases can ultimately provide catalytically competent species under hydrogen atmosphere, activation of Mn(I) pre-catalyst with hydride donor promoters, e.g. KHBEt3, dramatically improves catalytic performance of the system and eliminates induction times associated with slow catalyst activation.Manganese-based hydrogenation catalysts are sensitive to high temperatures and may degrade under industrially relevant conditions. Here, the authors report a highly efficient manganese pincer pre-catalyst displaying high TOF values (up to 41 000 h−1) and stability (TON up to 200 000) at loadings as low as 5-200 ppm. Any catalyst should be efficient and stable to be implemented in practice. This requirement is particularly valid for manganese hydrogenation catalysts. While representing a more sustainable alternative to conventional noble metal-based systems, manganese hydrogenation catalysts are prone to degrade under catalytic conditions once operation temperatures are high. Herein, we report a highly efficient Mn(I)-CNP pre-catalyst which gives rise to the excellent productivity (TOF° up to 41 000 h-1) and stability (TON up to 200 000) in hydrogenation catalysis. This system enables near-quantitative hydrogenation of ketones, imines, aldehydes and formate esters at the catalyst loadings as low as 5-200 p.p.m. Our analysis points to the crucial role of the catalyst activation step for the catalytic performance and stability of the system. While conventional activation employing alkoxide bases can ultimately provide catalytically competent species under hydrogen atmosphere, activation of Mn(I) pre-catalyst with hydride donor promoters, e.g. KHBEt3, dramatically improves catalytic performance of the system and eliminates induction times associated with slow catalyst activation.Any catalyst should be efficient and stable to be implemented in practice. This requirement is particularly valid for manganese hydrogenation catalysts. While representing a more sustainable alternative to conventional noble metal-based systems, manganese hydrogenation catalysts are prone to degrade under catalytic conditions once operation temperatures are high. Herein, we report a highly efficient Mn(I)-CNP pre-catalyst which gives rise to the excellent productivity (TOF° up to 41 000 h-1) and stability (TON up to 200 000) in hydrogenation catalysis. This system enables near-quantitative hydrogenation of ketones, imines, aldehydes and formate esters at the catalyst loadings as low as 5-200 p.p.m. Our analysis points to the crucial role of the catalyst activation step for the catalytic performance and stability of the system. While conventional activation employing alkoxide bases can ultimately provide catalytically competent species under hydrogen atmosphere, activation of Mn(I) pre-catalyst with hydride donor promoters, e.g. KHBEt3, dramatically improves catalytic performance of the system and eliminates induction times associated with slow catalyst activation. |
| ArticleNumber | 12 |
| Author | Müller, Christian Chernyshov, Ivan Yu van Schendel, Robin K. A. Filonenko, Georgy A. Pidko, Evgeny A. Yang, Wenjun Weber, Manuela |
| Author_xml | – sequence: 1 givenname: Wenjun orcidid: 0000-0002-4410-6398 surname: Yang fullname: Yang, Wenjun organization: Inorganic Systems Engineering group, Department of Chemical Engineering, Faculty of Applied Sciences, Delft University of Technology – sequence: 2 givenname: Ivan Yu surname: Chernyshov fullname: Chernyshov, Ivan Yu organization: TheoMAT Group, ChemBio cluster, ITMO University – sequence: 3 givenname: Robin K. A. surname: van Schendel fullname: van Schendel, Robin K. A. organization: Inorganic Systems Engineering group, Department of Chemical Engineering, Faculty of Applied Sciences, Delft University of Technology – sequence: 4 givenname: Manuela surname: Weber fullname: Weber, Manuela organization: Institute of Chemistry and Biochemistry, Freie Universität Berlin – sequence: 5 givenname: Christian surname: Müller fullname: Müller, Christian organization: Institute of Chemistry and Biochemistry, Freie Universität Berlin – sequence: 6 givenname: Georgy A. orcidid: 0000-0001-8025-9968 surname: Filonenko fullname: Filonenko, Georgy A. email: G.A.Filonenko@tudelft.nl organization: Inorganic Systems Engineering group, Department of Chemical Engineering, Faculty of Applied Sciences, Delft University of Technology – sequence: 7 givenname: Evgeny A. orcidid: 0000-0001-9242-9901 surname: Pidko fullname: Pidko, Evgeny A. email: E.A.Pidko@tudelft.nl organization: Inorganic Systems Engineering group, Department of Chemical Engineering, Faculty of Applied Sciences, Delft University of Technology |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/33397888$$D View this record in MEDLINE/PubMed |
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| PublicationDecade | 2020 |
| PublicationPlace | London |
| PublicationPlace_xml | – name: London – name: England |
| PublicationTitle | Nature communications |
| PublicationTitleAbbrev | Nat Commun |
| PublicationTitleAlternate | Nat Commun |
| PublicationYear | 2021 |
| Publisher | Nature Publishing Group UK Nature Publishing Group Nature Portfolio |
| Publisher_xml | – name: Nature Publishing Group UK – name: Nature Publishing Group – name: Nature Portfolio |
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| References_xml | – reference: FilonenkoGAvan PuttenRHensenEJPidkoEACatalytic (de) hydrogenation promoted by non-precious metals–Co, Fe and Mn: recent advances in an emerging fieldChem. Soc. Rev.201847145914831:CAS:528:DC%2BC1cXotFeitQ%3D%3D2933438810.1039/C7CS00334J – reference: PapaVEfficient and selective hydrogenation of amides to alcohols and amines using a well-defined manganese–PNN pincer complexChem. Sci.20178357635851:CAS:528:DC%2BC2sXjvVygtLc%3D30155202609271610.1039/C7SC00138J – reference: BuhaibehRPhosphine‐NHC manganese hydrogenation catalyst exhibiting a non‐classical metal‐ligand cooperative H2 activation modeAngew. Chem. Int. Ed.201958672767311:CAS:528:DC%2BC1MXmvVCnsL0%3D10.1002/anie.201901169 – reference: Clarke, M. L. & Widegren, M. B. in Homogeneous Hydrogenation with Non‐Precious Catalysts (ed. Teichert, J. F.). 111–140 (Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim, Germany, 2020). – reference: WeberSStögerBKirchnerKHydrogenation of nitriles and ketones catalyzed by an air-stable bisphosphine Mn (I) complexOrg. Lett.201820721272151:CAS:528:DC%2BC1cXitFWis7zN3039888310.1021/acs.orglett.8b03132 – reference: KallmeierFKempeRManganese complexes for (De) hydrogenation catalysis: a comparison to cobalt and iron catalystsAngew. Chem. Int. Ed.20185746601:CAS:528:DC%2BC2sXhvFensbjM10.1002/anie.201709010 – reference: EliassonSHHJensenVRBenefit of a hemilabile ligand in deoxygenation of fatty acids to 1-alkenesFaraday Discuss.20192202312482019FaDi..220..231H10.1039/C9FD00037B – reference: Rylander, P. N. 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| Snippet | Any catalyst should be efficient and stable to be implemented in practice. This requirement is particularly valid for manganese hydrogenation catalysts. While... Manganese-based hydrogenation catalysts are sensitive to high temperatures and may degrade under industrially relevant conditions. Here, the authors report a... |
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| SubjectTerms | 119/118 140/131 639/638/77/885 639/638/77/888 639/638/911/406/939 Aldehydes Carbonyl compounds Carbonyls Catalysis Catalysts Coordination compounds Esters Formate esters High temperature Humanities and Social Sciences Hydrogen storage Hydrogenation Imines Ketones Manganese multidisciplinary Noble metals Science Science (multidisciplinary) Stability |
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| Title | Robust and efficient hydrogenation of carbonyl compounds catalysed by mixed donor Mn(I) pincer complexes |
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