Recent advancements in the development of molecular organic photocatalysts

Bobo, M. Victoria; Kuchta, Joseph J.; Vannucci, Aaron K.

doi:10.1039/d1ob00396h

Cited by 68 publications

(32 citation statements)

References 106 publications

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“…Photoredox catalysts are increasingly attracting much attention because they can mediate new efficient organic reactions under mild conditions with light irradiation. 1–6 In general, excited photoredox catalysts can activate substrates via single electron transfer to generate radical cations or anions as reactive intermediates and to efficiently induce selective reactions, which are difficult to attain under thermal conditions.…”

Section: Introductionmentioning

confidence: 99%

Acridinium salts as photoredox organocatalysts for photomediated cationic RAFT and DT polymerizations of vinyl ethers

et al. 2022

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Section: Introductionmentioning

confidence: 99%

Acridinium salts as photoredox organocatalysts for photomediated cationic RAFT and DT polymerizations of vinyl ethers

et al. 2022

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“…In this case, although batch conditions were not directly transposable to flow conditions due to the presence of a precipitate, the replacement of KOH with a soluble base, DBU, allowed for this synthesis to be conducted in flow. In contrast to previous reactions, this method offers a green approach for the synthesis of piperazines through the use of a purely organic photoredox catalyst to promote the radical generation [10,[24][25][26][27][28]. The successful transition of this method from batch to continuous flow conditions offers another advantage over other methods.…”

Section: Snap Reagentsmentioning

confidence: 99%

“…Photoredox catalysis introduces sustainable and greener methods for chemical synthesis. However, due to the potential toxicity and cost associated with transition-metalcatalysts, recent research has been directed towards the use and development of organic photocatalysts [10,[24][25][26][27][28]. Organic photocatalysts offer significantly more sustainability as they can be synthesized from renewable organic materials.…”

Section: Organic Photoredox C-h Alkylationmentioning

confidence: 99%

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Recent Advances in the Synthesis of Piperazines: Focus on C–H Functionalization

Durand

Szostak

2021

Organics

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Piperazine ranks as the third most common nitrogen heterocycle in drug discovery, and it is the key component of several blockbuster drugs, such as Imatinib (also marketed as Gleevec) or Sildenafil, sold as Viagra. Despite its wide use in medicinal chemistry, the structural diversity of piperazines is limited, with about 80% of piperazine-containing drugs containing substituents only at the nitrogen positions. Recently, major advances have been made in the C–H functionalization of the carbon atoms of the piperazine ring. Herein, we present an overview of the recent synthetic methods to afford functionalized piperazines with a focus on C–H functionalization.

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“…Finally, we evaluate the feasibility of a cross-coupling reaction of an aryl chloride with N-methylpyrrole. Organocatalytic alternatives for photoredox catalysts have been developed to avoid the use of expensive Ir-and Ru-based systems and to tune the redox potential of the catalysts [5,[11][12][13]. Their synthetic potential has been illustrated by their applicability for a broad spectrum of substrates and in a range of reactions such as polymerizations, substitutions, bond cleavage reactions and cycloadditions [2,[14][15][16].…”

Section: Introductionmentioning

confidence: 99%

Photoredox-Catalyzed Reduction of Halogenated Arenes in Water by Amphiphilic Polymeric Nanoparticles

et al. 2021

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The use of organic photoredox catalysts provides new ways to perform metal-free reactions controlled by light. While these reactions are usually performed in organic media, the application of these catalysts at ambient temperatures in aqueous media is of considerable interest. We here compare the activity of two established organic photoredox catalysts, one based on 10-phenylphenothiazine (PTH) and one based on an acridinium dye (ACR), in the light-activated dehalogenation of aromatic halides in pure water. Both PTH and ACR were covalently attached to amphiphilic polymers that are designed to form polymeric nanoparticles with hydrodynamic diameter DH ranging between 5 and 11 nm in aqueous solution. Due to the hydrophobic side groups that furnish the interior of these nanoparticles after hydrophobic collapse, water-insoluble reagents can gather within the nanoparticles at high local catalyst and substrate concentrations. We evaluated six different amphiphilic polymeric nanoparticles to assess the effect of polymer length, catalyst loading and nature of the catalyst (PTH or ACR) in the dechlorination of a range of aromatic chlorides. In addition, we investigate the selectivity of both catalysts for reducing different types of aryl-halogen bonds present in one molecule, as well as the activity of the catalysts for C-C cross-coupling reactions. We find that all polymer-based catalysts show high activity for the reduction of electron-poor aromatic compounds. For electron-rich compounds, the ACR-based catalyst is more effective than PTH. In the selective dehalogenation reactions, the order of bond stability is C-Cl > C-Br > C-I irrespective of the catalyst applied. All in all, both water-compatible systems show good activity in water, with ACR-based catalysts being slightly more efficient for more resilient substrates.

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Recent advancements in the development of molecular organic photocatalysts

Abstract: A review on the recent advances of six classes of organic photocatalysts with respect to photophysical and redox properties.

Cited by 68 publications

References 106 publications

Acridinium salts as photoredox organocatalysts for photomediated cationic RAFT and DT polymerizations of vinyl ethers

Acridinium salts as photoredox organocatalysts for photomediated cationic RAFT and DT polymerizations of vinyl ethers

Recent Advances in the Synthesis of Piperazines: Focus on C–H Functionalization

Photoredox-Catalyzed Reduction of Halogenated Arenes in Water by Amphiphilic Polymeric Nanoparticles

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