Hybrid Metal Catalysts as Valuable Tools in Organic Synthesis: An Overview of the Recent Advances in Asymmetric C─C Bond Formation Reactions DOI Creative Commons
Isabella Rimoldi, Giulia Coffetti, Raffaella Gandolfi

et al.

Molecules, Journal Year: 2024, Volume and Issue: 29(21), P. 5090 - 5090

Published: Oct. 28, 2024

Carbon–carbon bond formation represents a key reaction in organic synthesis, resulting paramount importance for constructing the carbon backbone of molecules. However, traditional metal-based catalysis, despite its advantages, often struggles with issues related to efficiency, selectivity, and sustainability. On other hand, while biocatalysis offers superior selectivity due an extraordinary recognition process substrate, scope applicable reactions remains somewhat limited. In this context, Artificial Metalloenzymes (ArMs) Metallo Peptides (MPs) offer promising not fully explored solution, merging two fields transition metal catalysis biotransformations, by inserting catalytically active cofactor into customizable protein scaffold or coordinating ion directly short tunable amino acid (Aa) sequence, respectively. As result, these hybrid catalysts have gained attention as valuable tools challenging catalytic transformations, providing systems new-to-nature properties synthesis. This review overview recent advances development ArMs MPs, focusing on their application asymmetric carbon–carbon bond-forming reactions, such carbene insertion, Michael additions, Friedel–Crafts cross-coupling cyclopropanation, underscoring versatility synthesizing biologically relevant compounds.

Language: Английский

Cycloheptyl-fused-PNN-manganese catalyzed asymmetric transfer hydrogenation of ketones DOI
Zechen Wang, Shuo Zhang, Zhifeng Ma

et al.

Molecular Catalysis, Journal Year: 2024, Volume and Issue: 564, P. 114274 - 114274

Published: June 8, 2024

Language: Английский

Citations

10
The importance of alkali cations in manganese-catalyzed enantioselective transfer hydrogenation of ketones: An insight into the effect of “NH” and “C N” groups in ligands DOI
Zechen Wang, Yuanyuan Wang,

Quanming Lyu

et al.

Journal of Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 115998 - 115998

Published: Feb. 1, 2025

Language: Английский

Citations

1
Enhancing enantioselectivity of manganese catalyst for asymmetric transfer hydrogenation of ketones through P,N,N-chelation of a cyclooctyl pyridine DOI
Shuo Zhang, Zhifeng Ma,

Yulei Li

et al.

Journal of Catalysis, Journal Year: 2024, Volume and Issue: 437, P. 115682 - 115682

Published: July 31, 2024

Language: Английский

Citations

6
Manganese(Ⅰ)-Catalyzed Asymmetric (Transfer) Hydrogenation of Simple Ketones by a Novel Chiral Tridentate P*Nn Ligand DOI
Bin Li, Jingfeng Zhang,

Yu Ding

et al.

Published: Jan. 1, 2025

Language: Английский

Citations

0
Manganese-Catalyzed Asymmetric Hydrogenation of Pyridyl Cyclic N-Alkyl Imines: A Direct Route to S-Nicotine and Derivatives DOI
Jitao Yang, Yanan Guo, Zheng Wang

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: March 12, 2025

The asymmetric hydrogenation (AH) of cyclic N-alkyl imines offers an elegant and efficient method to afford chiral amines, especially for S-nicotine its derivatives. However, this approach remains ongoing challenge due undesirable coordination pyridyl-containing substrates the active metal catalyst. Herein, we disclose a manganese-catalyzed AH that allows access other α-(hetero)aryl pyrrolidines provides example base-metal catalyst displays superior performance noble counterparts.

Language: Английский

Citations

0
Enantioselective Synthesis of Chiral Fluorinated Amines via Manganese-Catalyzed Asymmetric Hydrogenation DOI

Xin‐Hu Hu,

Kaikai Zheng,

Hang Yin

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: March 28, 2025

A highly enantioselective Mn-catalyzed hydrogenation of fluorinated imines has been realized. The success this is attributed to the use chiral ferrocenyl P,N,N ligand bearing an additional center at pyridinylmethyl position. displayed broad functional group tolerance, thus furnishing a wide range optically active amines with up 98% enantiomeric excess. utility methodology well-demonstrated by scale-up asymmetric N-(4′-methoxyphenyl)-ethan-2,2,2-trifluoro-1-phenyl-1-imine.

Language: Английский

Citations

0
Asymmetric Transfer Hydrogenation of Ketones Improved by PNN–Manganese Complexes DOI
Yi‐Chang Su, Zhifeng Ma,

Jingyao Wang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(17), P. 12318 - 12325

Published: Aug. 15, 2024

Chiral manganese(I) complexes that contain carbocyclic-fused 8-amino-5,6,7,8-tetrahydroquinolinyl groups are appended with distinct para-R substituents have proven to be effective catalysts in the asymmetric transfer hydrogenation (ATH) of a wide range ketones (48 examples). Notably, Mn2 proved most productive catalyst, allowing an outstanding turnover number 8300 catalyst loadings as low 0.01 mol %. Furthermore, this catalytic protocol shows considerable promise for applications synthesis chiral drugs such Lusutrombopag.

Language: Английский

Citations

3
Manganese-Catalyzed Asymmetric Hydrogenation for Atroposelective Dynamic Kinetic Resolution of Heterobiaryl Ketone N-Oxides DOI

Yin-Bo Wan,

Xiang‐Ping Hu

ACS Catalysis, Journal Year: 2024, Volume and Issue: unknown, P. 17633 - 17641

Published: Nov. 15, 2024

An atroposelective dynamic kinetic resolution of configurationally labile heterobiaryl ketone N-oxides via Mn-catalyzed asymmetric hydrogenation has been disclosed. By use a structurally finely tuned chiral ferrocenyl P,N,N-ligand, the proceeds smoothly under mild conditions with simultaneous installation central and axial chirality, giving wide range atropisomeric 1-arylisoquinoline 2-arylpyridine bearing alcohol structure high diastereo- enantioselectivities. The diastereomer product could be readily prepared in stereospecific way complete inversion chirality Mitsunobu reaction. value this central- axial-chiral N-oxide scaffold is preliminarily demonstrated by its successful utility as catalyst allylation benzaldehyde allyltrichlorosilane.

Language: Английский

Citations

2
Cinchona alkaloids-derived chiral ligands for Mn-catalyzed ATH of ketones: Improvement of enantioselectivity through π-π stacking-induced hydrogen bond DOI
Lin Zhang,

Pinli Dai,

Xin Meng

et al.

Journal of Catalysis, Journal Year: 2024, Volume and Issue: 439, P. 115758 - 115758

Published: Sept. 14, 2024

Language: Английский

Citations

1
Revisiting the Reviewed: A Meta‐Analysis of Computational Studies on Transition Metal‐Catalysed Hydrogenation Reactions DOI Creative Commons

Michæl Bühl,

Shahbaz Ahmad

ChemCatChem, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 2, 2024

Abstract This review of reviews attempts to systematically analyze the recent advancements in transition metal‐catalyzed hydrogenation reactions as discussed previous articles, emphasizing computational insights that enhance our understanding reaction mechanisms. It highlights efficacy density functional theory (DFT) calculating free energies, exploring mechanistic pathways and kinetics processes and, focusing on substrates such alkenes, alkynes, amides, imines, nitriles, carbon dioxide. The details significant studies where models help predict outcomes aid catalyst design. Notable discussions include role solvent effects metal‐ligand interactions, which are crucial for reactivity selectivity but often underestimated models. concludes with current challenges prospects, suggesting enhanced experimental collaborations refine

Language: Английский

Citations

0