Organocatalytic activation of hydrogen peroxide: towards green and sustainable oxidations

Poursaitidis, Efthymios T.; Gkizis, Petros L.; Triandafillidi, Ierasia; Kokotos, Christoforos G.

doi:10.1039/d3sc05618j

Cited by 10 publications

(1 citation statement)

References 135 publications

(170 reference statements)

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“…1 While many effective oxidants are available, the employment of green oxidants such as hydrogen peroxide for the practical oxidation of organic substrates usually requires the use of a catalyst to activate hydrogen peroxide into an oxygen-transfer species which is kinetically more reactive. 2,3…”

Section: Introductionmentioning

confidence: 99%

Untangling the catalytic importance of the Se oxidation state in organoselenium-mediated oxygen-transfer reactions: the conversion of aniline to nitrobenzene

Madabeni,

Tanini,

Capperucci

et al. 2024

Chem. Sci.

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Section: Introductionmentioning

confidence: 99%

Untangling the catalytic importance of the Se oxidation state in organoselenium-mediated oxygen-transfer reactions: the conversion of aniline to nitrobenzene

Madabeni,

Tanini,

Capperucci

et al. 2024

Chem. Sci.

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Organocatalyzed Asymmetric Conjugate Addition of Alcohols to β‐Fluoroalkyl Vinylsulfones by Bifunctional Phosphonium Salt Catalyst

Luo,

Jiang,

Yang

et al. 2024

Chemistry A European J

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Chiral secondary alcohols, serving as essential structural motifs, hold significant potential for diverse applications. The exploration of effective synthetic strategies toward these compounds is both attractive and challenging. Herein, we present an asymmetric oxa‐Michael reaction involving aliphatic alcohols as nucleophiles and β‐fluoroalkyl vinylsulfones catalyzed by bifunctional phosphonium salt (BPS), achieving high yields and excellent enantioselectivities (up to 98% yield and 98% ee). Additionally, a sequential process including asymmetric oxa‐Michael and debenzylation, facilitated by BPS/Lewis acid cooperation, was revealed for synthesizing diverse chiral secondary alcohol compounds in high yields (81‐88%) with consistent stereoselectivities. Furthermore, mechanistic explorations and subsequent results unveiled that the enantioselectivity originates from hydrogen‐bonding and ion‐pair interactions between the BPS catalyst and the substrates.

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Photochemical Aerobic Upcycling of Polystyrene Plastics via Synergistic Indirect HAT Catalysis

Mountanea,

Skolia,

Kokotos

2024

Chemistry A European J

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Plastic pollution constitutes an evergrowing urgent environmental problem, since overaccumulation of plastic waste, arising from the immense increase of the production of disposable plastic products, overcame planet’s capacity to properly handle them. Chemical upcycling of polystyrene constitutes a convenient method for the conversion of plastic waste into high‐added value chemicals, suggesting an attractive perspective in dealing with the environmental crisis. We demonstrate herein a novel, easy‐to‐perform organocatalytic photoinduced aerobic protocol, which proceeds via synergistic indirect hydrogen atom transfer (HAT) catalysis under LED 390 nm Kessil lamps as the irradiation source. The developed method employs a BrCH2CN‐thioxanthone photocatalytic system and was successfully applied to a variety of everyday‐life plastic products, leading to the isolation of benzoic acid after simple base‐acid work up in yields varying from 23‐49%, while a large‐scale experiment was successfully performed, suggesting that the photocatalytic step is susceptible to industrial application.

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Organocatalytic activation of hydrogen peroxide: towards green and sustainable oxidations

Abstract: The advent of Organocatalysis provided an additional option in every researcher’s arsenal, towards the development of elegant and sustainable protocols for various organic transformations. Oxidation reactions are considered as key...

Cited by 10 publications

References 135 publications

Untangling the catalytic importance of the Se oxidation state in organoselenium-mediated oxygen-transfer reactions: the conversion of aniline to nitrobenzene

Untangling the catalytic importance of the Se oxidation state in organoselenium-mediated oxygen-transfer reactions: the conversion of aniline to nitrobenzene

Organocatalyzed Asymmetric Conjugate Addition of Alcohols to β‐Fluoroalkyl Vinylsulfones by Bifunctional Phosphonium Salt Catalyst

Photochemical Aerobic Upcycling of Polystyrene Plastics via Synergistic Indirect HAT Catalysis

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