Unveiling a key catalytic pocket for the ruthenium NHC-catalysed asymmetric heteroarene hydrogenation

Hamza, Andrea; Moock, Daniel; Schlepphorst, Christoph; Schneidewind, Jacob; Baumann, Wolfgang; Glorius, Frank

doi:10.1039/d1sc06409f

Cited by 12 publications

(14 citation statements)

References 86 publications

(31 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In addition to N-heterocycles, we applied our catalyst to the more challenging hydrogenation of O-and Sheterocycles. The selective hydrogenation of benzofurans is of great interest [9,18,19] because the associated products are important bio-active molecules. With our catalyst, we are able to selectively hydrogenate benzofuran to 2,3-dihydrobenzofuran (Scheme 2, product 28).…”

Section: Resultsmentioning

confidence: 99%

A Highly Active Cobalt Catalyst for the General and Selective Hydrogenation of Aromatic Heterocycles

Bauer

Müller

Keskin

et al. 2023

Chemistry A European J

View full text Add to dashboard Cite

Nanostructured earth abundant metal catalysts that mediate important chemical reactions with high efficiency and selectivity are of great interest. This study introduces a synthesis protocol for nanostructured earth abundant metal catalysts. Three components, an inexpensive metal precursor, an easy to synthesize N/C precursor, and a porous support material undergo pyrolysis to give the catalyst material in a simple, single synthesis step. By applying this catalyst synthesis, a highly active cobalt catalyst for the general and selective hydrogenation of aromatic heterocycles could be generated. The reaction is important with regard to organic synthesis and hydrogen storage. The mild reaction conditions observed for quinolines permit the selective hydrogenation of numerous classes of N‐, O‐ and S‐heterocyclic compounds such as: quinoxalines, pyridines, pyrroles, indoles, isoquinoline, aciridine amine, phenanthroline, benzofuranes, and benzothiophenes.

show abstract

Section: Resultsmentioning

confidence: 99%

A Highly Active Cobalt Catalyst for the General and Selective Hydrogenation of Aromatic Heterocycles

Bauer

Müller

Keskin

et al. 2023

Chemistry A European J

View full text Add to dashboard Cite

show abstract

“…[21] Indeed, various functionalized indoles were efficiently and selectively hydrogenated to the corresponding indolines with good yields. Apart from methyl-and ethyl-substituted indoles, halogen-containing substrates (F, Cl, Br) were well tolerated and gave the corresponding indolines in up to 86 % (Table 4, entries [1][2][3][4][5][6][7][8][9][10][11][12][13][14]. In addition, methoxy-and ester-containing indoles also reacted well and gave > 80 % of the desired products (Table 4, entries 15-22).…”

Section: Co-catalyzed Hydrogenation Of Indoles and Benzothiophenesmentioning

confidence: 99%

“…[3] However, compared to indoles, the hydrogenation of benzofurans is more challenging. [4] Hence, majority of catalysts applied for this hydrogenation reaction are based on homogeneous [5] and heterogeneous [6][7][8][9][10] precious metal catalytic systems (Scheme 1). In addition, few non-noble metal-based catalysts are used for the hydrogenation of only benzofuran without any substrate scope.…”

Section: Introductionmentioning

confidence: 99%

Development of a General and Selective Nanostructured Cobalt Catalyst for the Hydrogenation of Benzofurans, Indoles and Benzothiophenes

Zhou

Chandrashekhar

et al. 2023

Angewandte Chemie

View full text Add to dashboard Cite

The selective hydrogenation of benzofurans in the presence of a heterogeneous non‐noble metal catalyst is reported. The developed optimal catalytic material consists of cobalt‐cobalt oxide core–shell nanoparticles supported on silica, which has been prepared by the immobilization and pyrolysis of cobalt‐DABCO‐citric acid complex on silica under argon at 800 °C. This novel catalyst allows for the selective hydrogenation of simple and functionalized benzofurans to 2,3‐dihydrobenzofurans as well as related heterocycles. The versatility of the reported protocol is showcased by the reduction of selected drugs and deuteration of heterocycles. Further, the stability, recycling, and reusability of the Co‐nanocatalyst are demonstrated.

show abstract

“…Very recently, a detailed mechanistic study of a related asymmetric hydrogenation reaction catalysed Ru-L 24 has been reported. 120 Kuwano et al in 2016 reported the EH of azaindoles using a chiral catalyst prepared from [Ru(η 3 -methallyl) 2 (cod)] and a trans-chelating bis-phosphine ligand (L 25 ) (Table 19). 121 The…”

Section: Organic and Biomolecular Chemistry Reviewmentioning

confidence: 99%

“…Very recently, a detailed mechanistic study of a related asymmetric hydrogenation reaction catalysed Ru–L 24 has been reported. 120…”

Section: Transition Metal Complex-catalysed Asymmetric Hydrogenationmentioning

confidence: 99%

Recent developments in enantio- and diastereoselective hydrogenation of N-heteroaromatic compounds

Ramachandran

Goodyear²,

Silvestri³

et al. 2022

Org. Biomol. Chem.

View full text Add to dashboard Cite

show abstract

Unveiling a key catalytic pocket for the ruthenium NHC-catalysed asymmetric heteroarene hydrogenation

Abstract: The chiral ruthenium(II)bis-SINpEt complex is a versatile and powerful catalyst for the hydrogenation of a broad range of heteroarenes. This study aims to provide understanding of the active form of...

Cited by 12 publications

References 86 publications

A Highly Active Cobalt Catalyst for the General and Selective Hydrogenation of Aromatic Heterocycles

A Highly Active Cobalt Catalyst for the General and Selective Hydrogenation of Aromatic Heterocycles

Development of a General and Selective Nanostructured Cobalt Catalyst for the Hydrogenation of Benzofurans, Indoles and Benzothiophenes

Recent developments in enantio- and diastereoselective hydrogenation of N-heteroaromatic compounds

Contact Info

Product

Resources

About