Selective C(sp<sup>2</sup>)–H bond functionalization of olefins <i>via</i> visible-light-induced photoredox-quinuclidine dual catalysis

Gu, Xintao; Li, Longhai; Wei, Yin; Shi, Min

doi:10.1039/d2cc03694k

Cited by 5 publications

(4 citation statements)

References 49 publications

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“…The same group further utilized the quinuclidinium radical cation catalysis to realize the distal heteroaryl ipso-migration. [23] The reaction featured a simple operation with readily available starting materials, leading to alkenylheteroaromatic products 46 in good yields under mild conditions. A possible mechanism was proposed, as depicted in Scheme 11.…”

Section: Nitrogen Radical Catalysismentioning

confidence: 99%

Radical Covalent Catalysis: Recent Advances and Future Developments

Xiao

2023

ChemCatChem

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Section: Nitrogen Radical Catalysismentioning

confidence: 99%

Radical Covalent Catalysis: Recent Advances and Future Developments

Xiao

2023

ChemCatChem

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“…Thereafter, a related strategy was applied to the C(sp 2 )À H bond functionalization of unactivated alkene 15 via distal heteroaryl ipso-migration (Scheme 6A). [20] If the reaction is similarly initiated by the photoredox-catalyzed oxidation of OC-4 and the addition of OC-4A onto olefin 15, the subsequent steps are resolutely different (Scheme 6B). Indeed, the formation of radical adduct OC-4E is followed by an intramolecular radical addition onto the benzothiazole ring.…”

Section: Ammonium Radical Catalysismentioning

confidence: 99%

“…The cationic character of intermediate OC‐4D allows the release of precatalyst OC‐4 by a β‐elimination triggered by AcO − . Thereafter, a related strategy was applied to the C(sp 2 )−H bond functionalization of unactivated alkene 15 via distal heteroaryl ipso ‐migration (Scheme 6A) [20] . If the reaction is similarly initiated by the photoredox‐catalyzed oxidation of OC‐4 and the addition of OC‐4A onto olefin 15 , the subsequent steps are resolutely different (Scheme 6B).…”

Section: Ammonium Radical Catalysismentioning

confidence: 99%

Merging Organocatalysis and Photocatalysis: A New Momentum in Covalent Radical Catalysis

et al. 2023

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The use of free radicals as organocatalysts constitutes a powerful strategy to activate and functionalize unsaturated carbon chains. Indeed, the unique affinity of open‐shell species for alkenes and alkynes can be rerouted to achieve the catalytic covalent activation of the substrate and control a subsequent radical cascade. However, the field of covalent radical catalysis has remained confidential for decades due to important issue in terms of catalyst handling, reaction design and viability. Recently, these pitfalls have been addressed one by one by the use of photocatalysis to control the generation and the reactivity of radical catalysts. This Concept article aims to highlight recent achievements in the field of photocatalyzed covalent radical catalysis and the perspectives offered by such catalytic combinations. The reaction mechanisms and the interconnection between the catalytic cycles are notably discussed with the hope of demonstrating the synthetic potential of this approach and foster a rapid growth of this nascent topic.

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“…In this direction, porous polymeric support can prove beneficial for the effective mass transport of reactants and is expected to influence the catalytic efficiency. Quinuclidine derivatives have been explored to catalyze reactions in solution state; in this paper, immobilization of quinuclidine on a porous polymer microparticle-based solid substrate has been studied. − …”

Section: Introductionmentioning

confidence: 99%

Quinuclidine-Immobilized Porous Polymeric Microparticles as a Compelling Catalyst for the Baylis–Hillman Reaction

Kumar

Kuckling

Nebhani

2022

ACS Appl. Polym. Mater.

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Poly(quinuclidin-3-yl methacrylate-co-divinylbenzene) microparticles having porous as well as nonporous morphology and varying contents of quinuclidine functionality were synthesized by distillation−precipitation polymerization. Further, the synthesized microparticles were explored to catalyze the Baylis−Hillman reaction between 4-nitrobenzaldehyde and acrylonitrile. Porous and nonporous microparticles functionalized with a catalytic moiety with a loading of 70% (labeled as P 70 and NP 70 ) were employed to optimize reaction parameters such as water content, solvent, and temperature for the Baylis−Hillman reaction between 4-nitrobenzaldehyde and acrylonitrile. Using optimal conditions, the catalytic efficiency of porous and nonporous microparticles at different feed compositions was determined. Porous microparticles containing 70% of quinuclidine (P 70 ) displayed 100% conversion within 16 h at 50 °C, while nonporous microparticles containing 70% of quinuclidine (NP 70 ) displayed a relatively less catalytic conversion, which is attributed to their lower surface area. Furthermore, the catalytic activity of porous microparticles containing 70% of quinuclidine (P 70 ) for the Baylis−Hillman reaction involving a variety of aryl aldehyde derivatives was determined, where the microparticles displayed impressive catalytic efficiency. In addition, the reusability of the microparticles functionalized with a catalytic moiety was evaluated for five cycles of catalytic reaction.

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Selective C(sp²)–H bond functionalization of olefins via visible-light-induced photoredox-quinuclidine dual catalysis

Abstract: The site selective C(sp2)–H bond functionalization of olefins has been achieved through a visible-light-induced photoredox-quinuclidine dual catalysis upon merging quinuclidinium radical cation addition to alkene strategy and the distal heteroaryl...

Cited by 5 publications

References 49 publications

Radical Covalent Catalysis: Recent Advances and Future Developments

Radical Covalent Catalysis: Recent Advances and Future Developments

Merging Organocatalysis and Photocatalysis: A New Momentum in Covalent Radical Catalysis

Quinuclidine-Immobilized Porous Polymeric Microparticles as a Compelling Catalyst for the Baylis–Hillman Reaction

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Selective C(sp2)–H bond functionalization of olefins via visible-light-induced photoredox-quinuclidine dual catalysis

Abstract: The site selective C(sp2)–H bond functionalization of olefins has been achieved through a visible-light-induced photoredox-quinuclidine dual catalysis upon merging quinuclidinium radical cation addition to alkene strategy and the distal heteroaryl...

Cited by 5 publications

References 49 publications

Radical Covalent Catalysis: Recent Advances and Future Developments

Radical Covalent Catalysis: Recent Advances and Future Developments

Merging Organocatalysis and Photocatalysis: A New Momentum in Covalent Radical Catalysis

Quinuclidine-Immobilized Porous Polymeric Microparticles as a Compelling Catalyst for the Baylis–Hillman Reaction

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Selective C(sp²)–H bond functionalization of olefins via visible-light-induced photoredox-quinuclidine dual catalysis