A simple metal-free catalytic sulfoxidation under visible light and air

Gu, Xiangyong; Li, Xiang; Chai, Yahong; Yang, Qi; Li, Pixu; Yao, Yingming

doi:10.1039/c2gc36683e

Cited by 155 publications

(93 citation statements)

References 47 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Herein, selective sulfoxidation reaction, an extensively studied reaction by virtue of its critical role in pharmaceutical synthesis, fossil fuel desulfurization, and industrial waste-water treatment, [33,34] was performed to investigate the catalytic activity of CNO. Strongly oxidizing ROS, such as O 2…”

Section: Communication Inmentioning

confidence: 99%

Enhanced Singlet Oxygen Generation in Oxidized Graphitic Carbon Nitride for Organic Synthesis

et al. 2016

View full text Add to dashboard Cite

Experimental data reveal that the incorporation of carbonyl groups into polymer matrix can significantly enhance singlet oxygen ((1) O2 ) generation and suppress production of other reactive oxygen species. Excitonic processes investigated by phosphorescence spectroscopy reveal enhanced triplet-exciton generation in the modified g-C3 N4 , which facilitate (1) O2 generation through an energy transfer process. Benefiting from this, the modified g-C3 N4 shows excellent conversion and selectivity in organic synthesis.

show abstract

Section: Communication Inmentioning

confidence: 99%

Enhanced Singlet Oxygen Generation in Oxidized Graphitic Carbon Nitride for Organic Synthesis

et al. 2016

View full text Add to dashboard Cite

show abstract

“…The oxidation of sulfides containing other alkyl groups (cyclopropyl and allyl groups), instead of methyl group, was also possible (entries 5-6), without detection of benzaldehyde or other by-products as was found with other catalytic systems previously reported. [55] Interestingly, dialkyl sulfides (entries 7 and 8), including the sterically hindered tert-butylmethyl derivative (2 g), were efficiently oxidized to 3 g-h in shorter reaction times (entries 8-9). Moreover, the effectiveness of the crystalline material 1 b was evaluated in the oxidation of sulfide 2 i, which is known to be the precursor of the drug modafinil.…”

Section: Full Papersmentioning

confidence: 99%

Imine‐Based Covalent Organic Frameworks as Photocatalysts for Metal Free Oxidation Processes under Visible Light Conditions

et al. 2019

View full text Add to dashboard Cite

Photochemistry of extended polyimine COF structures with laminar, spherical and 3D architectures has been examined. We show that these materials, composed by undecorated phenyl rings and imine fragments, can act as photocatalyts in oxidative transformations, being the crystalline laminar material the most active photocatalyst. The sulfoxidation reaction proceeds with good yields for a large variety of different sulfides. This process was carried out under visible light conditions (20 W), ethanol/ H 2 O as solvent, and the heterogeneous porous material can be recycled up to 9 times. The crystallinity favours the behavior as photocatalyst of laminar and spherical COFs whereas any particular effect on the 3D material activity was observed. Sulfoxidation reaction mainly proceeds through an energy transfer mechanism using crystalline laminar material. In addition, these materials as photocatalysts were used for the oxidation of phenyl boronic acid into phenol. . a) Catalytic runs in the oxidation of sulfide 2 a to 3 a in nine consecutive 24 hours catalytic runs by addition of 0.3 mmol of sulfide 2 a after each cycle (see S.I. for further information). The output of the catalytic reaction is expressed as mmol of 3 a generated per cycle. Characterization after one catalytic cycle: b) SEM image of crystalline Laminar-COF 1 b c) FT-IR (black colour before catalysis and red colour after catalysis) d) PXRD (black colour before catalysis, red colour, after catalysis). Scheme 1. Mechanistic plausible scenarios for photocatalytic aerobic sulfoxidation reactions (PC = photocatalyst).

show abstract

“…[12,13] Previously, aerobic photooxidation of sulfides has been successfully accomplished by using metal complexes or organic dyes as PSs. Noteworthy systemsr eported recently used photosensitizers based on tetra-O-acetyl riboflavin, [2,9] Rose Bengal, [14] thioxanthones, [15] Pt II complexes, [16] Ru II Cu II complexes, [17] coenzyme NAD + , [18] and BODIPY dyes. [19] However,a sf ar as we know,I r III complexes have not been used in similars tudies and, furthermore, improvements can still be made in the field to shorten reactiont imes, enhance the photostability and recyclability of PSs, optimize the selectivity of the reaction, expandt he substrate scope, and avoid organic solvents and UV light.…”

Section: Introductionmentioning

confidence: 99%

Selective Photooxidation of Sulfides Catalyzed by Bis‐cyclometalated Ir^III Photosensitizers Bearing 2,2′‐Dipyridylamine‐Based Ligands

Vaquero

Ruiz-Riaguas

Martı́nez-Alonso

et al. 2018

Chemistry A European J

View full text Add to dashboard Cite

A new family of heteroleptic bis-cyclometalated Ir complexes with formula [Ir(CN^ ) (NN^ )]Cl (CN^ =2-phenylpyridinate and NN^ =2,2'-dipyridylamine or N-benzylated 2,2'-dipyridylamines, were synthesized, characterized, and successfully used as photosensitizers in the catalytic photooxidation of an array of dialkyl, dibenzyl, alkyl aryl, and diaryl sulfides, as well as sulfur-containing amino acids. Furthermore, the reactions proceeded with optimal chemoselectivity, and atom economy under mild conditions. Experimental observations support a dual mechanism in which singlet oxygen and superoxide are the actual oxidants.

show abstract

A simple metal-free catalytic sulfoxidation under visible light and air

Cited by 155 publications

References 47 publications

Enhanced Singlet Oxygen Generation in Oxidized Graphitic Carbon Nitride for Organic Synthesis

Enhanced Singlet Oxygen Generation in Oxidized Graphitic Carbon Nitride for Organic Synthesis

Imine‐Based Covalent Organic Frameworks as Photocatalysts for Metal Free Oxidation Processes under Visible Light Conditions

Selective Photooxidation of Sulfides Catalyzed by Bis‐cyclometalated Ir^III Photosensitizers Bearing 2,2′‐Dipyridylamine‐Based Ligands

Contact Info

Product

Resources

About

A simple metal-free catalytic sulfoxidation under visible light and air

Cited by 155 publications

References 47 publications

Enhanced Singlet Oxygen Generation in Oxidized Graphitic Carbon Nitride for Organic Synthesis

Enhanced Singlet Oxygen Generation in Oxidized Graphitic Carbon Nitride for Organic Synthesis

Imine‐Based Covalent Organic Frameworks as Photocatalysts for Metal Free Oxidation Processes under Visible Light Conditions

Selective Photooxidation of Sulfides Catalyzed by Bis‐cyclometalated IrIII Photosensitizers Bearing 2,2′‐Dipyridylamine‐Based Ligands

Contact Info

Product

Resources

About

Selective Photooxidation of Sulfides Catalyzed by Bis‐cyclometalated Ir^III Photosensitizers Bearing 2,2′‐Dipyridylamine‐Based Ligands