Visible-light-induced aerobic epoxidation with vitamin B2-based photocatalyst

Shen, Defang; Ren, Ting; Luo, Zundu; Sun, Feiyang; Han, Yaling; Chen, K.; Zhang, Xuan; Zhou, Min; Gong, Peiwei; Chao, Mianran

doi:10.1039/d3ob00663h

Cited by 6 publications

(2 citation statements)

References 33 publications

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“…2021 年, Cibulka 课题组 [41] 利用 RFT 为光催化剂, 将胺和醛偶联起来实现了叔酰胺的合成(Scheme 2022 年, 王晓磊课题组 [42] 以 RFT 为光催化剂, 以奎 [43] . 最近, 本课题组 [44] 以维生素 B2 或 RFT 为光催化剂, 以商品化 1,8-二氮杂双环[5. 4 [45] .…”

Section: 含氮官能团的单电子氧化unclassified

Advances in Flavin-Inspired Photocatalytic Oxidations Involving Single Electron Transfer Process

Shen,

Li,

Jing

et al. 2024

Chinese Journal of Organic Chemistry

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Section: 含氮官能团的单电子氧化unclassified

Advances in Flavin-Inspired Photocatalytic Oxidations Involving Single Electron Transfer Process

Shen,

Li,

Jing

et al. 2024

Chinese Journal of Organic Chemistry

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“…A conceptual leap in singlet oxygen chemistry would involve its use in the asymmetric oxidation of electron-poor substrates. [20] At the heart of our strategy is the in-situ preparation of the nucleophilic hydroperoxide 13 by photooxygenation of an excess of 2,3-dimethyl-2-butene 12 with B5. The alkene 12 has been selected for the in-situ generation of an hydroperoxide through photooxygenation due to the high quenching rate constant of 12 with singlet oxygen (k = 5.6 10 7 L mol À 1 s À 1 in CHCl 3 ) and the selective formation of 13 by 1 O 2 -mediated oxidation of 12.…”

Section: Dyementioning

confidence: 99%

Synthesis of BODIPY Organophotocatalysts by Boron Functionalization with Quinine Derivatives and Applications in Asymmetric Photooxygenation

Coutant,

Fischer,

Nun

et al. 2023

ChemistrySelect

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Boron dipyrromethene (BODIPY) derivatives are key dyes owing to their interesting (electro)chemical and spectroscopic properties. These features have been exploited in various scientific domains such as materials science, biomedicine or organic synthesis. In particular, heavy‐atom containing BODIPY photocatalysts have found widespread applications in photoredox and energy transfer catalysis. The covalent attachment of heavy atoms to the boron dipyrromethene core enables the population of the triplet state through intersystem crossing (ISC), which is involved in the generation of singlet oxygen via triplet‐triplet energy transfer. While the functionalization of the dipyrromethene core has been extensively studied, investigations on boron substitution is far less described. In this work, boron functionalization of diiodo‐BODIPY dyes has enabled the grafting of quinine derivatives leading to a new family of chiral photosensitizers. The photophysical properties and the photostability of these photocatalysts have been investigated in dichloromethane and methanol. Preliminary investigations in asymmetric photooxidative processes have demonstrated the synthetic potential of these BODIPY‐quinine dyes in photoorganocatalysis.

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Photochemical Synthesis and Ring‐Opening of Aziridines and Epoxides: State‐of‐the‐Art

Furniel,

Corrêa

2024

ChemPhotoChem

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The development of greener methods for the preparation of three‐membered rings has increased in the last decade, not only due to their biological activity, but also by the ring strain of those heterocycles that make them useful precursors of more complex molecules. In this work, the visible‐light‐promoted synthesis and ring‐opening of aziridines and epoxides, reported in the last five years, were reviewed. Both homogeneous and heterogeneous catalysts were discussed and, in addition, the plausible mechanism pathways were highlighted.

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Visible-light-induced aerobic epoxidation with vitamin B2-based photocatalyst

Abstract: Herein we described a catalytic epoxidation of α,β-enone with peroxide in situ generated via a predominant single electron transfer and a minor energy transfer pathways using inexpensive natural vitamin B2...

Cited by 6 publications

References 33 publications

Advances in Flavin-Inspired Photocatalytic Oxidations Involving Single Electron Transfer Process

Advances in Flavin-Inspired Photocatalytic Oxidations Involving Single Electron Transfer Process

Synthesis of BODIPY Organophotocatalysts by Boron Functionalization with Quinine Derivatives and Applications in Asymmetric Photooxygenation

Photochemical Synthesis and Ring‐Opening of Aziridines and Epoxides: State‐of‐the‐Art

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