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Organometallic Flow Chemistry pp 43–76Cite as

Organic Photoredox Chemistry in Flow

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Part of the book series: Topics in Organometallic Chemistry ((TOPORGAN,volume 57))

Abstract

The recent movement toward greener, more sustainable chemistry has led to the emergence of photoredox chemistry, capable of catalyzing a wide berth of chemical transformations by channeling the energy of light to reach otherwise unobtainable levels of reactivity and selectivity. A recent parallel development in the field of flow chemistry has led to the enhancement of reactivity and productivity of these photoredox processes, making it a practical method for organic synthesis. This chapter discusses recent advances in the field of organic photoredox chemistry whose reactivity or productivity has been enhanced by flow chemistry.

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Notes

  1. 1.

    For an overview of aerobic oxidations in continuous flow, see Pieber and Kappe [32].

  2. 2.

    They hypothesized that this was because of the more favorable reduction potential (E red3 = −1.51 eV vs. E red1 = −1.33 eV).

  3. 3.

    Two substrates were not accelerated in flow; however, these compounds were also problematic in batch.

Abbreviations

AIBN:

Azobisisobutyronitrile

bpy:

2,2′-Bipyridine

dF(CF3)ppy:

2-(2′,4′-Difluorophenyl)-5-trifluoromethylpyridine

dmb:

4,4′-Dimethyl-2,2′-dipyridine

DMF:

N,N-Dimethylformamide

dmp:

2,9-Dimethyl-1,10-phenanthroline

DMSO:

Dimethyl sulfoxide

DPEPhos:

Bis[(2-diphenylphosphino)phenyl]methane

DSSC:

Dye-sensitized solar cell

dtbbpy:

di-tert-Butylbipyridine

FEP:

Fluorinated ethylene propylene

HDF:

Hydrodefluorination

IC:

Interconversion

ISC:

Intersystem crossing

LED:

Light-emitting diode

OLED:

Organic light-emitting diode

PEEK:

Polyetheretherketone

PFA:

Polyfluoroalkoxy

ppy:

2,2′-Phenylpyridine

SET:

Single electron transfer

TFA:

Trifluoroacetic acid

THF:

Tetrahydrofuran

TMEDA:

N,N,N′,N′-Tetramethyl-1,2-diaminoethylene

TMS:

Trimethylsilyl

TOF:

Turnover frequency

UV:

Ultraviolet

Xantphos:

4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene

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Authors and Affiliations

  1. Department of Biomolecular Systems, Max Planck Institute of Colloids and Interfaces, Am Mühlenberg 1, 14195, Potsdam, Germany

    Matthew B. Plutschack, Camille A. Correia, Peter H. Seeberger & Kerry Gilmore

  2. FreieUniversität Berlin, Institute of Chemistry and Biochemistry, Arnimallee 22, 14195, Berlin, Germany

    Peter H. Seeberger

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  1. Matthew B. Plutschack
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  2. Camille A. Correia
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  3. Peter H. Seeberger
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  4. Kerry Gilmore
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Correspondence to Kerry Gilmore .

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Editors and Affiliations

  1. Micro Flow Chemistry and Process Technology, Eindhoven University of Technology, Eindhoven, The Netherlands

    Timothy Noël

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Plutschack, M.B., Correia, C.A., Seeberger, P.H., Gilmore, K. (2015). Organic Photoredox Chemistry in Flow. In: Noël, T. (eds) Organometallic Flow Chemistry. Topics in Organometallic Chemistry, vol 57. Springer, Cham. https://doi.org/10.1007/3418_2015_155

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