Solid Materials as Sources for Synthetically Useful Singlet Oxygen

Wahlen, Joos; Vos, Dirk De; Jacobs, Pierre; Alsters, Paul L.

doi:10.1002/adsc.200303224

Cited by 112 publications

(63 citation statements)

References 86 publications

(81 reference statements)

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“…For this reason, reactions occurring between organic molecules (mainly in a singlet state) and ground-state O 2 to produce new singlet compounds are generally forbidden by the Wigners spin selection rule. [ 32,33 ] Intuitively, we can deduce a hypothesis that groundstate O 2 has to be activated to a high-energy state and in turn participate in oxidation reactions.…”

Section: Doi: 101002/adma201502068mentioning

confidence: 99%

Palladium‐Based Nanomaterials: A Platform to Produce Reactive Oxygen Species for Catalyzing Oxidation Reactions

et al. 2015

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Oxidation reactions by molecular oxygen (O2 ) over palladium (Pd)-based nanomaterials are a series of processes crucial to the synthesis of fine chemicals. In the past decades, investigations of related catalytic materials have mainly been focused on the synthesis of Pd-based nanomaterials from the angle of tailoring their surface structures, compositions and supporting materials, in efforts to improve their activities in organic reactions. From the perspective of rational materials design, it is imperative to address the fundamental issues associated with catalyst performance, one of which should be oxygen activation by Pd-based nanomaterials. Here, the fundamentals that account for the transformation from O2 to reactive oxygen species over Pd, with a focus on singlet O2 and its analogue, are introduced. Methods for detecting and differentiating species are also presented to facilitate future fundamental research. Key factors for tuning the oxygen activation efficiencies of catalytic materials are then outlined, and recent developments in Pd-catalyzed oxygen-related organic reactions are summarized in alignment with each key factor. To close, we discuss the challenges and opportunities for photocatalysis research at this unique intersection as well as the potential impact on other research fields.

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Section: Doi: 101002/adma201502068mentioning

confidence: 99%

Palladium‐Based Nanomaterials: A Platform to Produce Reactive Oxygen Species for Catalyzing Oxidation Reactions

et al. 2015

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“…[52] At higher pH values, however, molybdate(VI) catalyzes the disproportionation of alkaline aqueous H 2 O 2 ; the reaction is known as a "dark" generation of singlet oxygen. [53] Most studies were performed under controlled pH conditions to prevent this disproportionation of H 2 O 2 as a side reaction in molybdenum(VI)-catalyzed oxidative halogenation. One option is to use AcOH as a reaction medium, as demonstrated by an ammonium molybdate catalyzed oxidative bromination of phenols, anilines, and their derivatives in high yields (Scheme 5).…”

Section: Vanadium and Molybdenum Complexes As Functional Mimics Of Vamentioning

confidence: 99%

Oxidative Halogenation with “Green” Oxidants: Oxygen and Hydrogen Peroxide

2009

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It is difficult to imagine organic chemistry without organo-halogen compounds and the molecular halogens needed for their preparation. The halogens have very different reactivity, with iodine usually requiring some form of activation, while others are reactive and hazardous chemicals. To avoid their use, various modified reagents have been discovered (N-bromo- and N-chlorosuccinimide, Selectfluor..), but halogens are used to prepare these reagents and when they are used the atom economy is poor. A better approach, which is based on biomimetric research on oxidative halogenation in nature, consists of generating the halogenating reagent in situ under acidic conditions from a halide salt. The result of such a reaction has been halogenation with 100 % halogen atom economy. Suitable oxidants for the oxidation of halides are hydrogen peroxide and oxygen.

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“…One of them, juglone (11), is the starting material for several synthetic pathways. Although juglone can be obtained by thermal conditions, 25 photooxygenation of 1,5-dihydroxynaphthalene (8) is an attractive route for its synthesis.…”

Section: Photooxygenation Experimentsmentioning

confidence: 99%