Visible-Light-Promoted Asymmetric Catalysis by Chiral Complexes of First-Row Transition Metals

Li, Yanjun; Ye, Ziqi; Cai, Jiaxin; Gong, Lei

doi:10.1055/a-1344-2473

Cited by 16 publications

(2 citation statements)

References 49 publications

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“…Asymmetric photoredox catalysis has demonstrated immense promise in building novel chiral architectures by integrating photoredox catalysis with transition-metal-based asymmetric catalysis, organocatalysis, or enzyme catalysis . Despite these advancements, photochemical approaches for the reductive coupling of two unsaturated bonds are very limited, probably due to the complexities involved in suppressing side reactions involving high-energy intermediates, such as radicals and radical ions .…”

Section: Introductionmentioning

confidence: 99%

Asymmetric Cross-Coupling of Aldehydes with Diverse Carbonyl or Iminyl Compounds by Photoredox-Mediated Cobalt Catalysis

Chi,

Liao,

Cheng

et al. 2024

J. Am. Chem. Soc.

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The asymmetric cross-coupling of unsaturated bonds, hampered by their comparable polarity and reactivity, as well as the scarcity of efficient catalytic systems capable of diastereo-and enantiocontrol, presents a significant hurdle in organic synthesis. In this study, we introduce a highly adaptable photochemical cobalt catalysis framework that facilitates chemoand stereoselective reductive cross-couplings between common aldehydes with a broad array of carbonyl and iminyl compounds, including N-acylhydrazones, aryl ketones, aldehydes, and α-keto esters. Our methodology hinges on a synergistic mechanism driven by photoredox-induced single-electron reduction and subsequent radical−radical coupling, all precisely guided by a chiral cobalt catalyst. Various optically enriched β-amino alcohols and unsymmetrical 1,2-diol derivatives (80 examples) have been synthesized with good yields (up to 90% yield) and high stereoselectivities (up to >20:1 dr, 99% ee). Of particular note, this approach accomplishes unattainable photochemical asymmetric transformations of aldehydes with disparate carbonyl partners without reliance on any external photosensitizer, thereby further emphasizing its versatility and cost-efficiency.

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Section: Introductionmentioning

confidence: 99%

Asymmetric Cross-Coupling of Aldehydes with Diverse Carbonyl or Iminyl Compounds by Photoredox-Mediated Cobalt Catalysis

Chi,

Liao,

Cheng

et al. 2024

J. Am. Chem. Soc.

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“…Traditional TiO 2 - or ZnO-based materials have been studied for a long time as photocatalysts due to their exceptional merits of high electron mobility, high stability, non-toxicity, and low cost. However, both substances have relatively high band gap energies that can only be activated by UV irradiation, limiting their potential applications within the wavelength range of sunlight [ 6 , 7 , 8 , 9 ].…”

Section: Introductionmentioning

confidence: 99%

Magnetic CoFe1.95Y0.05O4-Decorated Ag3PO4 as Superior and Recyclable Photocatalyst for Dye Degradation

Liu

Meng

et al. 2023

Materials

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The Ag3PO4/CoFe1.95Y0.05O4 nanocomposite with magnetic properties was simply synthesized by the hydrothermal method. The structure and morphology of the prepared material were characterized, and its photocatalytic activity for degradation of the methylene blue and rhodamine B dyes was also tested. It was revealed that the Ag3PO4 in the nanocomposite exhibited a smaller size and higher efficiency in degrading dyes than the individually synthesized Ag3PO4 when exposed to light. Furthermore, the magnetic properties of CoFe1.95Y0.05O4 enabled the nanocomposite to possess magnetic separation capabilities. The stable crystal structure and effective degradation ability of the nanocomposite were demonstrated through cyclic degradation experiments. It was shown that Ag3PO4/CoFe1.95Y0.05O4–0.2 could deliver the highest activity and stability in degrading the dyes, and 98% of the dyes could be reduced within 30 min. Additionally, the photocatalytic enhancement mechanism and cyclic degradation stability of the magnetic nanocomposites were also proposed.

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Visible Light‐Induced Enantioselective Radical Reactions Catalyzed by Redox‐Active Chiral Lewis Acids

Cao,

Hong

2024

ChemCatChem

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This Concept outlines cutting‐edge progress in catalytic and enantioselective radical reactions facilitated by redox‐active chiral Lewis acids upon visible light excitation. These catalytic systems exploit the high reactivity of radical species to enable efficient stereocontrolled radical recombination. We delve into the design, underlying mechanisms, and practical applications of these catalysts, aiming for precise stereocontrolled bond formation. The synergistic blend of chirality and reactivity has brought a new level of precision to enantioselective radical additions, reshaping the approach to asymmetric synthesis. This Concept focuses on the recent progress and effective application of redox‐active chiral Lewis acids, including Rh, Ir, Ga and Ni, in catalyzing enantioselective radical reactions, which offers a comprehensive perspective on modern methods and projecting future directions in enantioselective radical chemistry.

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Visible-Light-Promoted Asymmetric Catalysis by Chiral Complexes of First-Row Transition Metals

Cited by 16 publications

References 49 publications

Asymmetric Cross-Coupling of Aldehydes with Diverse Carbonyl or Iminyl Compounds by Photoredox-Mediated Cobalt Catalysis

Asymmetric Cross-Coupling of Aldehydes with Diverse Carbonyl or Iminyl Compounds by Photoredox-Mediated Cobalt Catalysis

Magnetic CoFe1.95Y0.05O4-Decorated Ag3PO4 as Superior and Recyclable Photocatalyst for Dye Degradation

Visible Light‐Induced Enantioselective Radical Reactions Catalyzed by Redox‐Active Chiral Lewis Acids

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