Photoredox Catalytic Activation of CarbonHalogen Bonds: CH Functionalization Reactions under Visible Light

Bardagi, Javier Ivan; Ghosh, Indrajit

doi:10.1002/9783527808175.ch4

Visible Light‐Active Photocatalysis 2018

DOI: 10.1002/9783527808175.ch4

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Photoredox Catalytic Activation of CarbonHalogen Bonds: CH Functionalization Reactions under Visible Light

Javier Ivan Bardagi

Indrajit Ghosh

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Cited by 3 publications

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“…From our analysis, we could anticipate that other polyaromatic catalysts that follow a conPET mechanism such as 9,10-dicyanoanthracene (DCA) and rhodamine 6G , might be affected by the presence of water in the same way. Reactions using DCA as catalyst instead of NDI support this hypothesis (Table , entries 7 and 8).…”

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confidence: 95%

“…Environmentally friendly methodologies are readily available through photocatalysis having light as a clean reagent and giving the catalysis an opportunity to reduce residual waste. Advances in visible light photoredox catalysis have opened multiple approaches for the synthesis of organic compounds, which share the activation of reactive compounds by photoinduced single electron transfer (PET). − …”

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confidence: 99%

“…Intriguing by the effect of water on our previous study, we decided to explore how its addition impacts the yield of product at different catalyst loadings. Following our prior work conditions, 21 a mixture of 4-bromobenzonitrile (1) (as radical precursor), benzene (as radical acceptor), N,Ndiisopropylethylamine (DIPEA) (as sacrificial electron donor), and 2,7-dihexylbenzo[lmn] [3,8]phenanthroline-1,3,6,8-(2H,7H)-tetrone 21,35 (NDI, Scheme S4) as catalyst was evaluated in acetonitrile (ACN) and a mixture with water (Table 1).…”

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confidence: 99%

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Unravelling the Effect of Water Addition in Consecutive Photocatalysis with Naphthalene Diimide

2022

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We describe the effect of water addition in the catalyst performance for a C−H functionalization of benzene. Improved yields and selectivity were achieved in a consecutive photoredox catalysis in contrast to the reaction without water. Mechanistic analysis demonstrated this is due to a better catalyst stability and faster kinetic rather than a change in the different steps of the mechanism. The addition of water constitutes a convenient approach to improve catalyst performance, and it was also observed with other catalysts.

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confidence: 99%

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confidence: 99%

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Unravelling the Effect of Water Addition in Consecutive Photocatalysis with Naphthalene Diimide

2022

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Acridine Orange Hemi(Zinc Chloride) Salt as a Lewis Acid‐Photoredox Hybrid Catalyst for the Generation of α‐Carbonyl Radicals

2021

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A readily accessible organic‐inorganic hybrid catalyst is reported for the reductive fragmentation of α‐halocarbonyl compounds. The robust hybrid catalyst is a self‐stabilizing combination of ZnCl2 Lewis acid and acridine orange as the photoactive organic dye. Mechanistic specifics of this hybrid catalyst have been studied in detail using both photophysical and electrochemical experiments. A systematic study enabled the discovery of the appropriate Lewis acid for the effective LUMO stabilization of α‐halocarbonyl compounds and thereby lowering of reduction potential within the range of a standard organic dye. This strategy resolves the issues like dehalogenative hydrogenation or homo‐coupling of alkyl radicals by guiding the photoredox cycle through an oxidative quenching pathway. The cooperativity between the photoactive organic dye and the Lewis acid counterparts empowers functionalization with a wide range of coupling partners through efficient and controlled generation of alkyl radicals and serves as an appropriate alternative to the expensive late transition metal‐based photocatalysts. To demonstrate the application potential of this cooperative catalytic system, four different synthetic transformations of α‐carbonyl bromides were explored with broad substrate scopes.

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Excitation of Radical Anions of Naphthalene Diimides in Consecutive‐ and Electro‐Photocatalysis**

et al. 2021

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Both photo-and electrochemical transformations represent excellent opportunities for the development of environmentally friendly methodologies which, if combined, would result in improved methodologies. Thus, we present here a family of naphthalene diimide photocatalysts comparing a "pure" photochemical and an electro-photochemical transformation; by means of a CÀ H substitution in (hetero)aromatic systems with CÀ C bond formation. We identify a system that has the potential to be applied in both approaches with minor changes in the reaction conditions and recognize the excitation of radical anion of naphthalene diimides as the key event. Both approaches produce similar yields and reaction rates, although a consecutive photoinduced electron transfer (conPET) process shows in principle a simpler setup and more tolerance to a poor catalyst solubility, the electro-PET process improves selectivity and gives more room for optimization. The more accessible "pure" photochemical approach could be used as an initial assessment for photocatalytic transformation and electrophotocatalytic transformation.

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Photoredox Catalytic Activation of CarbonHalogen Bonds: CH Functionalization Reactions under Visible Light

Cited by 3 publications

References 64 publications

Unravelling the Effect of Water Addition in Consecutive Photocatalysis with Naphthalene Diimide

Unravelling the Effect of Water Addition in Consecutive Photocatalysis with Naphthalene Diimide

Acridine Orange Hemi(Zinc Chloride) Salt as a Lewis Acid‐Photoredox Hybrid Catalyst for the Generation of α‐Carbonyl Radicals

Excitation of Radical Anions of Naphthalene Diimides in Consecutive‐ and Electro‐Photocatalysis**

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