Photocatalytic benzylic C–H bond oxidation with a flavin scandium complex

Mühldorf, Bernd; Wolf, Robert

doi:10.1039/c5cc00178a

Cited by 116 publications

(70 citation statements)

References 26 publications

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“…Some derivatives were also immobilized on silica gel and applied in the oxidation of benzyl alcohols [13]. Furthermore, it was shown that the oxidation power of RFTA can be increased by coordination to scandium triflate [14]. Recently, the E / Z -isomerization of olefins with riboflavin as catalyst was reported [15], which was also used for cyclization to form coumarins [16].…”

Section: Resultsmentioning

confidence: 99%

Solvent-free, visible-light photocatalytic alcohol oxidations applying an organic photocatalyst

Obst¹,

König²

2016

Beilstein J. Org. Chem.

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A method for the solvent-free photocatalytic conversion of solid and liquid substrates was developed, using a novel rod mill apparatus. In this setup, thin liquid films are realized which is crucial for an effective photocatalytic conversion due to the low penetration depth of light in heterogeneous systems. Several benzylic alcohols were oxidized with riboflavin tetraacetate as photocatalyst under blue light irradiation of the reaction mixture. The corresponding carbonyl compounds were obtained in moderate to good yields.

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Section: Resultsmentioning

confidence: 99%

Solvent-free, visible-light photocatalytic alcohol oxidations applying an organic photocatalyst

Obst¹,

König²

2016

Beilstein J. Org. Chem.

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“…Because the E red * of 1 (RFl‐2Sc 3+ )* is 2.45 V versus SCE, which is higher than the one‐electron oxidation potential of toluene (2.20 V vs. SCE), the photocatalytic oxidation of toluene by O 2 occurs efficiently by using RFl‐2Sc 3+ as a photocatalyst to yield benzaldehyde (71 % yield). However, no photocatalytic oxidation of toluene by O 2 occurs in the presence of RFl without Sc 3+ …”

Section: Flavin Photoredox Catalystsmentioning

confidence: 99%

Effects of Lewis Acids on Photoredox Catalysis

et al. 2017

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The reactivityo fo rganic photoredox catalysts in oxidation reactions is enhanced by the addition of Lewis acids, which bind to the catalyst to increasei ts oxidizing ability.R edox-inactivem etal ions, such as Sc 3 + ,a lso act as Lewis acids and can bind to flavins to increaset heir oneelectron reduction potentials and photocatalytic stability. The Sc 3 + ion can bind to acridine and pyrene to enhance their photoredox catalytic activity in the oxidation of substrates by dioxygen. The binding of Lewis acids to radical anions enhances their overall photocatalytic activity by prohibitingab ack electron transfer from the radicala nions of substrates to the oxidized photocatalysts.T he photocatalytic asymmetrico xidationo ft erminal olefins by using water as the oxygen source with am ononuclear nonheme chiral manganese complex has been made possible by the addition of acetic acid, which is essential to afford the products with high enantioselectivity.[a] Prof.Scheme3.Quantitative measureo ft he Lewis acidity (DE)a nd ionic radius of redox-inactive metal ions.

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“…In addition, a series of elegant methods were successfully applied to construct C=O, C=C, and C=N double bonds (Scheme B). The direct oxidation of benzylic C(sp 3 )—H bond to aryl ketone was the most common . In 2012, Zhang and Patel accomplished a Pd‐catalyzed benzylic C(sp 3 )—H arylation/oxidation reaction.…”

Section: Background and Originality Contentmentioning

confidence: 99%

Copper‐Catalyzed Benzylic C—H Functionalization, Oxidation and Cyclization of Methylarenes: Direct Access to 2‐Arylbenzothiazoles

Jiang

2019

Chin. J. Chem.

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Summary of main observation conclusion The direct C—H functionalization of methylarenes is of great significance. Herein, a copper‐catalyzed oxidative C—N/C—S bond formation through benzylic C(sp3)—H functionalization, oxidation and cyclization of methylarenes is reported. Various 2‐arylbenzothiazoles have been synthesized in moderate to excellent yields with readily available o‐iodoaniline, potassium sulfide, and methylarenes as raw materials.

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Photocatalytic benzylic C–H bond oxidation with a flavin scandium complex

Abstract: The enhanced reduction potential of riboflavin tetraacetate coordinating to scandium triflate enables the challenging photocatalytic C-H oxidation of electron-deficient alkylbenzenes and benzyl alcohols.

Cited by 116 publications

References 26 publications

Solvent-free, visible-light photocatalytic alcohol oxidations applying an organic photocatalyst

Solvent-free, visible-light photocatalytic alcohol oxidations applying an organic photocatalyst

Effects of Lewis Acids on Photoredox Catalysis

Copper‐Catalyzed Benzylic C—H Functionalization, Oxidation and Cyclization of Methylarenes: Direct Access to 2‐Arylbenzothiazoles

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