Catalyst-free and visible light promoted trifluoromethylation and perfluoroalkylation of uracils and cytosines

Huang, Yang; Lei, Yun-Yun; Zhao, Liang; Gu, Jiwei; Yao, Qiuli; Wang, Ze; Li, Xiaofei; Zhang, Xingang; He, Chun‐Yang

doi:10.1039/c8cc07759b

Cited by 58 publications

(24 citation statements)

References 58 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…43 In 2018, Huang et al employed visible-light to prepare 5trifluoromethylated/perfluoroalkylated uracils 15.3 using inexpensive perfluoroalkyl iodides as fluoroalkylating reagents (Scheme 15). 44 Initially, the effect of various bases was explored in the trifluoromethylation of uracil in the solution of CF 3 I in DMSO. Results showed that Cs 2 CO 3 was a better choice than other bases, such as DMPU and TMEDA, which were commonly used as electron-donors in previous reports.…”

Section: ■ Introductionmentioning

confidence: 99%

Catalyst-Free Organic Transformations under Visible-Light

Tavakolian

Hosseini‐Sarvari

2021

ACS Sustainable Chem. Eng.

View full text Add to dashboard Cite

Pollutants from industry and chemical laboratories have harmful effects on human health and the environment. Concerns about this problem have led to the development of more versatile and sustainable protocols based on the principles of green chemistry. One of these innovative approaches is to carry out the reactions under visible-light sources without photocatalysts. This benign, simple, and cost-effective method, inspired by nature, could be a suitable alternative to some classical methods, and change the harsh reaction conditions into milder ones. In this Perspective, we outlined the results of catalyst-free organic reactions under visible-light to further encourage researchers in this promising field. The proposed mechanisms based on the generation of an electron donor−acceptor complex (EDA) and a single-electron transfer (SET) pathway were discussed.

show abstract

Section: ■ Introductionmentioning

confidence: 99%

Catalyst-Free Organic Transformations under Visible-Light

Tavakolian

Hosseini‐Sarvari

2021

ACS Sustainable Chem. Eng.

View full text Add to dashboard Cite

show abstract

“…Fluoro-containing enaminones are important motifs in medicines, agrochemicals, and chemical materials. In 2018, Li, Zhang, He, and co-workers 60 developed a photocatalytic, metal-free method for the direct room temperature perfluoroalkylation of enaminones including uracils, cytosines, and pyridinones (Scheme 32). This photocatalytic strategy allowed the installation of various perfluoroalkyl groups onto enaminones and derivatives in the absence of a transition-metal catalyst, with high functional group tolerance and excellent chemo-and regioselectivity.…”

Section: Photocatalytic C-h Bond Perfluoroalkylationmentioning

confidence: 99%

Recent Advances in Photoinduced Perfluoroalkylation Using Perfluoroalkyl Halides as the Radical Precursors

Tang¹,

Liu²,

Liu³

et al. 2022

Synthesis

View full text Add to dashboard Cite

Perfluoroalkylation is one of the most important methods for the introduction of multiple fluorine atoms into organic molecules in a single step. The use of photoinduced technology is a common strategy that uses the outstanding oxidation or reduction ability of a photoredox catalyst in its excited state to generate perfluoroalkyl radicals from perfluoroalkyl halides. The perfluoroalkyl radicals thus obtained can undergo various subsequent reactions under mild conditions, such as ATRA reaction of alkenes, alkynes, and 1,n-enynes; carbo/heteroperfluoroalkylation of alkenes and isocyanides; and C–H/F perfluoroalkylation. This allows the expedient incorporation of various perfluoroalkyl groups into the molecular motifs. Perfluorinated functional groups are still in demand in pharmaceutical and material sciences; this short review discusses recent advances in photoinduced perfluoroalkylation methodologies and technologies.1 Introduction2 Photocatalytic Perfluoroalkylation of Alkenes, Alkynes, and 1,n- Enynes3 Photocatalytic Carboperfluoroalkylation or Heteroperfluoroalkylation of Alkenes, Alkynes, Isocyanides, and Hydrazones4 Photocatalytic ATRE Reactions of Alkenes with Perfluoroalkyl Halides5 Photocatalytic C–X (X = H, F) Bond Perfluoroalkylation6 Continuous Flow Strategies in Photocatalytic Perfluoroalkylation7 Conclusions

show abstract

“…Very recently, non-covalent interaction initiated fluoroalkylation reaction has emerged as an attractive strategy [37][38][39][40][41][42][43][44][45][46][47]. Inspired by our previous studies in this field [48][49][50][51], we envision that if the solvent can serve as an electron donor compound, the reactions would be simpler. Here, we demonstrate a…”

Section: Introductionmentioning

confidence: 99%

Visible-light Promoted Atom Transfer Radical Addition−Elimination (ATRE) Reaction for the Synthesis of Fluoroalkylated Alkenes Using DMA as Electron-donor

Wang

Mao

et al. 2020

Molecules

Self Cite

View full text Add to dashboard Cite

Here, we describe a mild, catalyst-free and operationally-simple strategy for the direct fluoroalkylation of olefins driven by the photochemical activity of an electron donor−acceptor (EDA) complex between DMA and fluoroalkyl iodides. The significant advantages of this photochemical transformation are high efficiency, excellent functional group tolerance, and synthetic simplicity, thus providing a facile route for further application in pharmaceuticals and life sciences.Molecules 2020, 25, 508 2 of 8 mild, catalyst-free and operationally-simple strategy for the direct fluoroalkylation of olefins driven by the photochemical activity of electron donor−acceptor (EDA) complex between DMA and fluoroalkyl iodides. The significant advantages of this photochemical transformation are high efficiency, excellent functional group tolerance, and synthetic simplicity [52].

show abstract

Catalyst-free and visible light promoted trifluoromethylation and perfluoroalkylation of uracils and cytosines

Abstract: Here, we report a mild, catalyst-free and operationally simple strategy for the direct perfluoroalkylation of uracils, cytosines and pyridinones through a visible-light induced pathway.

Cited by 58 publications

References 58 publications

Catalyst-Free Organic Transformations under Visible-Light

Catalyst-Free Organic Transformations under Visible-Light

Recent Advances in Photoinduced Perfluoroalkylation Using Perfluoroalkyl Halides as the Radical Precursors

Visible-light Promoted Atom Transfer Radical Addition−Elimination (ATRE) Reaction for the Synthesis of Fluoroalkylated Alkenes Using DMA as Electron-donor

Contact Info

Product

Resources

About