Cooperative photoredox and palladium catalysis: recent advances in various functionalization reactions

Shee, Maniklal; Singh, N. D. Pradeep

doi:10.1039/d0cy02071k

Cited by 39 publications

(27 citation statements)

References 133 publications

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“…Dual photoredox/transition-metal catalysis has recently been widely employed as an important strategy for solving the problem of enantioselectivity encountered in radical and photochemistry . Using a dual photoredox/palladium catalytic system, our group achieved the highly enantioselective allylic alkylation of allyl acetates . In addition, Ding and coworkers developed a unique spiroketal-based bis(phosphine) (SKP) ligand and disclosed S N 2-type enantioselective substitutions of MBH adducts catalyzed by palladium .…”

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confidence: 99%

Enantioselective Radical S_N2-Type Alkylation of Morita–Baylis–Hillman Adducts Using Dual Photoredox/Palladium Catalysis

et al. 2021

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An enantioselective radical alkylation of 4-alkyl-1,4-dihydropyridines with Morita–Baylis–Hillman (MBH) adducts has been reported. The SN2-type products are predominant. This reaction is enabled by dual photoredox/palladium catalysis. The alkylation products are provided in good yields with good regio- and enantioselectivity. The use of Ding’s spiroketal-based bis(phosphine) (SKP) ligand is crucial to achieving satisfactory regio- and enantioselectivity. The resultant α,β-unsaturated ester can be easily reduced to a synthetically useful chiral allyl alcohol.

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confidence: 99%

Enantioselective Radical S_N2-Type Alkylation of Morita–Baylis–Hillman Adducts Using Dual Photoredox/Palladium Catalysis

et al. 2021

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“…Pd-catalyzed allylations are universally recognized as a powerful synthetic tool. Pd chemistry started being considerably influenced by the renewal of photochemistry, notably due to the availability of oxidation states that were not often considered in mechanistic proposals like transitory Pd(III) or Pd(IV) intermediates. , Yu and co-workers have recently reported the interesting incidence of photoredox catalysis on the regioselectivity as compared to classical Tsuji–Trost allylation where the nucleophile (p K a > 25) underwent external nucleophilic attack at the cationic Pd(II) allyl intermediate. Reactions with hard nucleophiles were much less investigated .…”

Section: Chiral Transition-metal-catalyzed Asymmetric Radical Processesmentioning

confidence: 99%

Enantioselective Radical Reactions Using Chiral Catalysts

Mondal¹,

et al. 2022

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Scheme 24 Enantioselective Radical Hydroacylation of Enals with α-Ketoacids byMerging Photoredox Catalysis with Amine Catalysis.Jang et al. exploited enantioselective tandem Michael addition/oxyamination of α,β-unsaturated aldehydes by combining asymmetric iminium catalysis using organocatalyst with photoinduced SOMO catalysis using N719/TiO2. 60 Here, TiO2 acts as a second cooperative photocatalyst along with Ru photocatalyst N719 which bound to the latter, increases the enantio-and diastereoselectivity of the process. Adamantane carboxylic acid (30 mol%) was used as an additive which promotes formation of iminium ion 2.1.48A from aldehyde 2.1.48 and chiral amine catalyst. This iminium intermediate then reacts with diethyl malonate to provide intermediate 2.1.48B which either undergoes hydrolysis to form β-substituted aldehyde 2.1.50 or photo-oxidation by the photoexcited Ru(II) dye to form enamine radical 2.1.48C. Subsequent addition of TEMPO to radical intermediate 2.1.48BC followed by hydrolysis afforded the desired product 2.1.49 (Scheme 25). This mechanism is obeying to a polar/radical crossover sequence where the first stereocontrol arises from the addition of the malonate.Recently, Bach group reported promising preliminary results of enantioselective [2+2] photocycloaddition of cinnamaldehyde in the presence of ruthenium photocatalyst and proline derived organocatalyst. 61

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“…In order to diversify treatments and avoid, as far as possible, the development of resistances, new approaches are focusing on noble metal nanoparticles. In this regard, palladium is one of the six platinum-group elements, a noble metal whose extraordinary catalytic activity [ 17 , 18 , 19 , 20 ] and capacity to stabilize a wide diversity of matter, confers it great versatility, being commonly used in the biomedical field as part of cancer therapy, in dentistry devices, and in probes for analyte detection, among others [ 21 , 22 ]. In recent years, its outstanding antibacterial capacity has also attracted widespread interest [ 22 , 23 , 24 ].…”

Section: Introductionmentioning

confidence: 99%

Palladium Nanoparticles Synthesized by Laser Ablation in Liquids for Antimicrobial Applications

et al. 2022

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Antibiotic resistance is a leading cause of death worldwide. In this paper, we explore new alternatives in the treatment of infections. Noble metal nanoparticles could help to mitigate this problem. In this work, palladium nanoparticles were synthesized by laser ablation in order to explore their antimicrobial capacity. To obtain palladium nanoparticles, a palladium plate immersed in water, or methanol, was ablated, using two pulsed lasers that emit radiation with wavelengths of 532 nm and 1064 nm, respectively. Pure Pd-NPs with crystalline microstructure and rounded shape were obtained. The nanoparticles’ size is more homogeneous if the laser wavelength is 532 nm, and it decreases when methanol is used as solvent, reaching mean diameters smaller than 6 nm. With the objective of studying antimicrobial activity against Staphylococcus aureus, the Pd-NPs were immobilized on the surface of titanium discs. The release of palladium ions was recorded during the first seven days, and the cytotoxicity of the immobilized NPs was also tested with L929 mouse fibroblast cell line. Palladium nanoparticles synthesized by means of the infrared laser in methanol showed a strong inhibitory effect on S. aureus and good cytocompatibility, with no toxic effect on fibroblast cells.

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Cooperative photoredox and palladium catalysis: recent advances in various functionalization reactions

Abstract: Cooperative photoredox and palladium catalysis for various functionalization reactions.

Cited by 39 publications

References 133 publications

Enantioselective Radical S_N2-Type Alkylation of Morita–Baylis–Hillman Adducts Using Dual Photoredox/Palladium Catalysis

Enantioselective Radical S_N2-Type Alkylation of Morita–Baylis–Hillman Adducts Using Dual Photoredox/Palladium Catalysis

Enantioselective Radical Reactions Using Chiral Catalysts

Palladium Nanoparticles Synthesized by Laser Ablation in Liquids for Antimicrobial Applications

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Cooperative photoredox and palladium catalysis: recent advances in various functionalization reactions

Abstract: Cooperative photoredox and palladium catalysis for various functionalization reactions.

Cited by 39 publications

References 133 publications

Enantioselective Radical SN2-Type Alkylation of Morita–Baylis–Hillman Adducts Using Dual Photoredox/Palladium Catalysis

Enantioselective Radical SN2-Type Alkylation of Morita–Baylis–Hillman Adducts Using Dual Photoredox/Palladium Catalysis

Enantioselective Radical Reactions Using Chiral Catalysts

Palladium Nanoparticles Synthesized by Laser Ablation in Liquids for Antimicrobial Applications

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Enantioselective Radical S_N2-Type Alkylation of Morita–Baylis–Hillman Adducts Using Dual Photoredox/Palladium Catalysis

Enantioselective Radical S_N2-Type Alkylation of Morita–Baylis–Hillman Adducts Using Dual Photoredox/Palladium Catalysis