New Roles for Photoexcited Eosin Y in Photochemical Reactions

Yan, Dongmei; Chen, Jia‐Rong; Xiao, Wen‐Jing

doi:10.1002/anie.201811102

Cited by 140 publications

(80 citation statements)

References 25 publications

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“…Scheme Catalytic cycle for the Minisci alkylation of azines through cerium photocatalysis Scheme 7 C − H functionalization of gaseous alkanes via cerium photocatalysis Eosin Y is a common organic photocatalyst in photoredox catalysis because the excited T 1 state formed under visible light irradiation (green light) acts as a one-electron transfer agent under basic conditions [60]. Recently, two new reactivity modes of excited state Eosin Y were reported [61]. [62], while Wu and coworkers discovered Eosin Y can act as a direct hydrogen atom transfer (HAT) catalyst under neutral conditions.…”

Section: − H Functionalization In Flow C − C Bond Formation C − H Amentioning

confidence: 99%

Pushing the boundaries of C–H bond functionalization chemistry using flow technology

2020

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C-H functionalization chemistry is one of the most vibrant research areas within synthetic organic chemistry. While most researchers focus on the development of small-scale batch-type transformations, more recently such transformations have been carried out in flow reactors to explore new chemical space, to boost reactivity or to enable scalability of this important reaction class. Herein, an up-to-date overview of C-H bond functionalization reactions carried out in continuous-flow microreactors is presented. A comprehensive overview of reactions which establish the formal conversion of a C-H bond into carbon-carbon or carbonheteroatom bonds is provided; this includes metal-assisted C-H bond cleavages, hydrogen atom transfer reactions and C-H bond functionalizations which involve an S E-type process to aromatic or olefinic systems. Particular focus is devoted to showcase the advantages of flow processing to enhance C-H bond functionalization chemistry. Consequently, it is our hope that this review will serve as a guide to inspire researchers to push the boundaries of C-H functionalization chemistry using flow technology.

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Section: − H Functionalization In Flow C − C Bond Formation C − H Amentioning

confidence: 99%

Pushing the boundaries of C–H bond functionalization chemistry using flow technology

2020

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“…[94][95][96][97][98][99][100][101][102][103][104][105] Particularly, visible-light photoredox catalysis is an ideal tool to initiate radical cascade reactions for the synthesis of heterocycles. [106][107][108][109][110][111][112][113][114][115][116][117][118] In 2017, Hong's group reported a visible-light-enabled radical strategy to synthesize spiroepoxy chroman-4-one derivatives 74 via a tandem oxidation/radical cyclization/epoxidation process (Scheme 14). [119] The optimal conditions involving the use of Ru(bpy) 3 Cl 2 ·6H 2 O, TBHP, and K 2 CO 3 in iPrOAc at room temperature with irradiation of blue LEDs demonstrated broad substrate scope and good functional group tolerance with respect to both 2-(allyloxy)arylaldehydes 72 and (2-(allyloxy)aryl)methanols 73.…”

Section: Visible-light-promoted Reactionsmentioning

confidence: 99%

“…In the past decade, visible‐light promoted organic synthesis has emerged as a highly economical and eco‐friendly strategy for the construction of various chemical bonds under mild conditions . Particularly, visible‐light photoredox catalysis is an ideal tool to initiate radical cascade reactions for the synthesis of heterocycles . In 2017, Hong's group reported a visible‐light‐enabled radical strategy to synthesize spiroepoxy chroman‐4‐one derivatives 74 via a tandem oxidation/radical cyclization/epoxidation process (Scheme ) .…”

Section: Radical Strategies For the Synthesis Of 3‐substituted Chrmentioning

confidence: 99%

Radical Reactions for the Synthesis of 3‐Substituted Chroman‐4‐ones

Xiong

Wei

et al. 2020

Eur J Org Chem

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Radical cascade cyclizations of o‐allyloxybenzaldehydes have emerged as a powerful strategy for the synthesis of 3‐substituted chroman‐4‐ones. This minireview summarizes the incorporation of various functional groups into the C3‐position of chroman‐4‐ones by employing appropriate radical precursors through transition‐metal‐free systems, silver‐catalyzed systems, or visible‐light‐promoted systems.

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“…Spectral data matched those in the literature. 22 [BSPIM] OTf. 1-Butylimidazole (1.06 mL, 8.05 mmol) and 1,3-propanesultone (0.702 mL, 8.05 mmol) were dissolved in toluene (2.0 mL), and stirred at 60 C for 24 h. The mixture was cooled to 25 C. The precipitate was washed with ether and toluene to remove non-ionic residues, and dried in vacuo.…”

Section: Synthesis Of Rtilsmentioning

confidence: 99%

Chemical Analysis of Ionic Liquids Using Photoelectron Spectroscopy

Seo

Park

2016

Bulletin Korean Chem Soc

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The feasibility of utilizing X-ray photoelectron spectroscopy (XPS) to analyze room-temperature ionic liquids (RTILs) was investigated in this study. Conventionally, the chemical structure of organic compounds is identified by nuclear magnetic resonance (NMR) spectroscopy. The properties of RTILs, especially their low vapor pressure, make it possible to analyze RTILs by using XPS. The usefulness of XPS on RTILs was confirmed by commercial RTILs. All atoms in RTILs were detected in survey XPS spectra, and the calculated atomic percentages matched well with theoretical values. After the verification of commercial RTILs by XPS, we synthesized three RTILs and investigated them with XPS. The atomic ratio and chemical environment of carbon in RTILs were verified by XPS. By adapting XPS to the investigation of RTILs, carbon atoms in different chemical environments were distinguishable by the binding energy shift, and the atomic ratio of the constituent atoms was identifiable after peak deconvolution. In addition, inorganic constituents were detected by XPS unlike in the case of NMR spectroscopy.

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New Roles for Photoexcited Eosin Y in Photochemical Reactions

Abstract: Neutral eosin Y‐derived photoexcited states have been found to serve as photoacids and direct hydrogen atom transfer (HAT) catalysts in the activation of glycals and C−H bonds, respectively. These studies pave the way for further use of eosin Y in photochemical synthesis.

Cited by 140 publications

References 25 publications

Pushing the boundaries of C–H bond functionalization chemistry using flow technology

Pushing the boundaries of C–H bond functionalization chemistry using flow technology

Radical Reactions for the Synthesis of 3‐Substituted Chroman‐4‐ones

Chemical Analysis of Ionic Liquids Using Photoelectron Spectroscopy

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