The Morita–Baylis–Hillman reaction for non-electron-deficient olefins enabled by photoredox catalysis

Shi, Min; Li, Longhai; Wei, Yin; Wei, Hao-Zhao

doi:10.1039/d1sc06784b

Cited by 15 publications

(12 citation statements)

References 49 publications

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“…In 2022, Shi's group developed a quinuclidinium radical catalyzed Morita‐Baylis‐Hillman (MBH) reaction for non‐electron‐deficient olefines (Scheme 10). [22] This strategy overcame the longstanding limitation of the MBH reaction, which is only suitable to electron‐deficient olefins. The key intermediate β ‐quinuclidinium radical, generated in situ by the addition of olefins with quinuclidinium radical cations, were applied to enable the MBH reaction of non‐electron‐deficient alkenes.…”

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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“…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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“…Unfortunately, the target product was not observed (Table , entries 1–3). Shi and co-workers reported that quinuclidine reagents can activate the non-electron-deficient olefins or enable new radical transformations. Encouraged by this work, we selected tertiary amines with rigid structures, such as DABCO and quinuclidine.…”

mentioning

confidence: 99%

Visible-Light-Mediated NHC and Tertiary Amine Catalysis Enabling α-H Acylation of Alkenes

Wang

Feng

et al. 2023

Org. Lett.

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An intermolecular direct α-C–H acylation of alkenes was revealed by the visible-light-mediated N-heterocyclic carbene and quinuclidine catalysis. This convenient protocol provides a facile synthesis toward novel natural products and drug derivatives of α-substituted vinyl ketones. Mechanistic investigations indicated that the transformation proceeded via sequential radical addition, radical coupling, and an elimination process.

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The Morita–Baylis–Hillman reaction for non-electron-deficient olefins enabled by photoredox catalysis

Abstract: A strategy for overcoming the limitation of the Morita-Baylis-Hillman (MBH) reaction, which is only applicable to electron-deficient olefins, has been achieved via visible-light induced photoredox catalysis in this report. A...

Cited by 15 publications

References 49 publications

Radical Covalent Catalysis: Recent Advances and Future Developments

Radical Covalent Catalysis: Recent Advances and Future Developments

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

Visible-Light-Mediated NHC and Tertiary Amine Catalysis Enabling α-H Acylation of Alkenes

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