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Search for "eosin Y" in Full Text gives 51 result(s) in Beilstein Journal of Organic Chemistry.

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Flow photochemistry: Old light through new windows

Jonathan P. Knowles,
Luke D. Elliott and
Kevin I. Booker-Milburn

Beilstein J. Org. Chem. 2012, 8, 2025–2052, doi:10.3762/bjoc.8.229

]. Photocatalysis can also be performed by using visible light. This has been applied to the hydrodehalogenation of α-haloketones by using the dye Eosin Y (36) as a photocatalyst, and both DIPEA and Hantzsch ester 35 as electron donors (Scheme 13). The reaction was shown to be high yielding for a number of

entirely unsuccessful under batch conditions to be conducted [54]. Eosin Y (36) catalysis was also applied to an organocatalytic (42) photoredox α-alkylation of octanal (40, Scheme 15) to aldehyde 43. The reaction proved to be high yielding under both batch and microflow conditions, and a reduced

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Graphical Abstract

Figure 1: An immersion-well batch reactor with 125 W medium pressure Hg lamp.

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Figure 2: Transmission profile of a 0.05 M solution, ε = 200 M⁻¹ cm⁻¹.

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Figure 3: Schematic of a typical microflow photochemical reactor (above) and detail of a triple-channel micro...

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Figure 4: Schematic of a typical macroflow photochemical reactor (above) and images of the FEP photochemical ...

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Scheme 1: [2 + 2] photocycloadditions of enones with enol derivatives.

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Scheme 2: Competing reactions in an intramolecular [2 + 2] photocycloaddition.

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Scheme 3: Diastereocontrolled cycloaddition of a cyclic enone with cyclopentene.

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Scheme 4: Comparison of yields and reaction times for a batch reactor with a microflow system.

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Scheme 5: Intramolecular [2 + 2] photocycloaddition.

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Scheme 6: Paterno–Büchi reaction of benzophenone with an allylic alcohol.

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Scheme 7: Photooxygenation of cyclopentadiene.

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Scheme 8: Preparation of the anthelmintic ascaridole 23.

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Scheme 9: Production of rose oxide 27 from (−)-β-citronellol (24).

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Scheme 10: Photocatalytic alkylation of benzylamine.

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Scheme 11: Photocatalytic reduction of 4-nitroacetophenone.

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Scheme 12: Conversion of L-lysine to L-pipecolinic acid.

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Scheme 13: Photocatalytic hydrodehalogenation.

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Scheme 14: Photocatalytic aza-Henry reactions.

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Scheme 15: Photocatalytic α-alkylation of aliphatic ketones.

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Scheme 16: Decarboxylative photochemical additions.

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Scheme 17: Photochemical addition of isopropanol to furanones.

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Scheme 18: Photochemical addition of methanol to limonene.

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Scheme 19: Light-promoted reduction of flavone.

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Scheme 20: Photoreduction of benzophenone with benzhydrol.

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Scheme 21: Barton reaction in a microflow system.

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Scheme 22: Microflow synthesis of vitamin D₃.

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Scheme 23: photochemical chlorination of cyclohexane.

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Scheme 24: photochemical cyanation of pyrene.

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Scheme 25: Intermolecular [2 + 2] cycloaddition of maleimide (76) and intramolecular [2 + 2] cycloaddition of ...

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Scheme 26: Intramolecular [5 + 2] cycloaddition of maleimide under flow conditions.

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Scheme 27: Intramolecular [5 + 2] cycloaddition as a key step in the synthesis of (±)-neostenine.

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Scheme 28: In situ generation of a thioaldehyde by photolysis of a phenacyl sulfide.

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Scheme 29: Photodimerisation of maleic anhydride.

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Scheme 30: [2 + 2] cycloaddition of a chiral enone with ethylene.

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Scheme 31: Intramolecular [2 + 2] cycloaddition of a cyclopentenone.

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Scheme 32: Photochemical Wolff rearrangement and cyclisation to β-lactams.

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Scheme 33: Photochemical rearrangement of aryl azides.

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Scheme 34: Rearrangement of quinoline N-oxides to quinolones.

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Scheme 35: Photochemical rearrangement of cyclobutenones.

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Scheme 36: Photoisomerisation en route to a vitamin-D derivative.

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Scheme 37: Schematic of the Seeberger photooxygenation apparatus and sensitised photooxygenation of citronello...

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Scheme 38: Sensitised photooxygenation of dihydroartemisinic acid.

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Scheme 39: Photochemical preparation of CpRu(MeCN)₃PF₆.

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Scheme 40: In situ photochemical generation and reaction of a [CpRu]⁺ catalyst.

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Scheme 41: Intermolecular alkene–alkyne coupling with photogenerated catalyst.

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Scheme 42: PET deoxygenation of nucleosides.

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Scheme 43: Photochemical defluorination of DABFT.

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Scheme 44: Aromatic azide reduction by visible-light-mediated photocatalysis.

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Scheme 45: Examples of visible-light-mediated reactions.

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Scheme 46: Visible-light-mediated formation of iminium ions.

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Scheme 47: Examples of visible-light-mediated photocatalytic reactions.

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Scheme 48: Anhydride formation from a visible-light-mediated process.

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Scheme 49: Light-mediated conjugate addition of glycosyl bromide 141 to acrolein.

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Scheme 50: Visible-light-mediated photocyclisation to [5]helicene.

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Album

Review

Published 21 Nov 2012

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