The mechanism of visible light-induced C–C cross-coupling by C<sub>sp<sup>3</sup></sub>–H bond activation

Maity, Bholanath; Dutta, Sayan; Cavallo, Luigi

doi:10.1039/d2cs00960a

Cited by 28 publications

(10 citation statements)

References 117 publications

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“…arylketones, tetrabutylammonium decatungstate, mesoporous graphitic carbon nitride), are also applicable for the HAT process. 7,8 By these tactics, a wide range of inert substrates with Csp3-H bonds serve as competent coupling partners. In a parallel strategy, by leveraging halogen atom transfer (XAT) mediator (e.g.…”

Section: Template For Synthesis Thiemementioning

confidence: 99%

Photoactive Ni-Complexes in Metallaphotoredox Catalysis: A Successful Match in C–C Cross-Coupling Reactions

Zhu,

Feng,

Dang

2024

Synthesis

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Nickel catalysis is a well-established and powerful tool for C–C cross-coupling reactions, and its versatility has expanded significantly over past decades by its combination with visible-light photocatalysis in metallaphotoredox chemistry. Photocatalysis enables the activation of traditionally inert substrates and turnover of the Ni catalyst through a single-electron transfer processes. In recent years, dual catalysis has been further empowered by photoactive Ni intermediates, which exhibit distinct reactivity profiles from their ground states and complement existing protocols. This short review focuses on the emergent subclass of metallaphotoredox catalysis in which the synergy of a photoactive Ni catalyst and a typical photocatalyst (e.g., a polypyridyl Ir complex) provide solutions to challenging C–C bond formation.1 Introduction2 Photoactive Nickel Complexes3 HAT-Mediated C–C Cross-Coupling4 Halofunctionalization of π-Systems5 Photoelimination of an Aryl Radical6 Conclusion

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Section: Template For Synthesis Thiemementioning

confidence: 99%

Photoactive Ni-Complexes in Metallaphotoredox Catalysis: A Successful Match in C–C Cross-Coupling Reactions

Zhu,

Feng,

Dang

2024

Synthesis

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“…This allows for greater flexibility in shaping a reactivity pattern that converts given substrates into desired products. [21] As research in this area continues, these reactions hold considerable potential for sustainable and efficient methodologies.…”

Section: Introductionmentioning

confidence: 99%

Visible Light‐Induced Photoredox and Copper‐Catalyzed C−N Cross‐Coupling: A Mechanistic Perspective

Talekar,

Dutta,

Mane

et al. 2024

Eur J Org Chem

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The formation of C−N bonds is a vital technique in organic synthesis for creating nitrogen‐containing motifs, which has extensive uses in agrochemicals, pharmaceuticals, and natural products. Significant progress has been made in constructing C−N bonds using transition metal catalysis. Nevertheless, utilizing alkyl substrates for the formation of Csp3−N bonds is a notable challenge. Synergistic photoredox and copper catalysis have proven to be a powerful tool to tackle this challenge. The development of this research domain is still in its early stages owing to the chemical and technical complexities of this catalytic process. This review attempts to summarize in‐depth mechanistic understanding of the photoredox/copper dual catalysed C−N coupling reactions taking into consideration of recently reported experimental and theoretical studies.

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“…Radical decarboxylation of carboxylic acid has held great significance in organic synthesis due to facile conversion of the formed radical intermediates to various high-value chemical products since Hunsdiecker et al discovered the radical decarboxylation of carboxylic acid derivatives. , Recently, visible-light photocatalysis provides a useful alternative and is emerging as a uniquely powerful tool in organic synthesis. − The implementation of photocatalytic strategies in radical decarboxylation reactions of carboxylic acids has resulted in substantial advancements. In particular, since the pioneering work of MacMillan, Waser, Lei, Xiao, and others, the direct construction of C–C or C–X bonds through the photocatalytic radical decarboxylation of carboxylic acids has been developed (Scheme A). − …”

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confidence: 99%

Photocatalytic Radical Decarboxylation [4 + 3] Annulation Reactions of Lactones via Dienoic Acid EDA Complexes

Wang,

Liang,

et al. 2024

ACS Sustainable Chem. Eng.

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The process of radical decarboxylation is crucial in organic synthesis. Nevertheless, decarboxylation of dienoic acids presents a greater challenge compared to that of aliphatic carboxylic acids. Herein, catalyst-and additive-free visible-lightpromoted [4 + 3] annulation of lactones and diamines was achieved via radical decarboxylation of dienoic acids. By means of this novel EDA-activated [4 + 3] annulation, the 1,5benzodiazepines, which display a wide range of biological activities and are widely used in many fields, can be directly accessed in high yields under mild conditions. This visible-light-induced radical decarboxylation [4 + 3] annulation tolerates a broad array of functional groups and intricate molecules, including pharmaceutical-relevant compounds and natural products.

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The mechanism of visible light-induced C–C cross-coupling by C_sp³–H bond activation

Abstract: The chemistry and the reaction mechanisms behind the four catalytic protocols currently available for visible light-induced C–C cross-coupling by activation of Csp3–H bonds are described.

Cited by 28 publications

References 117 publications

Photoactive Ni-Complexes in Metallaphotoredox Catalysis: A Successful Match in C–C Cross-Coupling Reactions

Photoactive Ni-Complexes in Metallaphotoredox Catalysis: A Successful Match in C–C Cross-Coupling Reactions

Visible Light‐Induced Photoredox and Copper‐Catalyzed C−N Cross‐Coupling: A Mechanistic Perspective

Photocatalytic Radical Decarboxylation [4 + 3] Annulation Reactions of Lactones via Dienoic Acid EDA Complexes

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The mechanism of visible light-induced C–C cross-coupling by Csp3–H bond activation

Abstract: The chemistry and the reaction mechanisms behind the four catalytic protocols currently available for visible light-induced C–C cross-coupling by activation of Csp3–H bonds are described.

Cited by 28 publications

References 117 publications

Photoactive Ni-Complexes in Metallaphotoredox Catalysis: A Successful Match in C–C Cross-Coupling Reactions

Photoactive Ni-Complexes in Metallaphotoredox Catalysis: A Successful Match in C–C Cross-Coupling Reactions

Visible Light‐Induced Photoredox and Copper‐Catalyzed C−N Cross‐Coupling: A Mechanistic Perspective

Photocatalytic Radical Decarboxylation [4 + 3] Annulation Reactions of Lactones via Dienoic Acid EDA Complexes

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The mechanism of visible light-induced C–C cross-coupling by C_sp³–H bond activation