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Photochemical Synthesis of Heterocycles: Merging Flow Processing and Metal-Catalyzed Visible Light Photoredox Transformations

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Flow Chemistry for the Synthesis of Heterocycles

Part of the book series: Topics in Heterocyclic Chemistry ((TOPICS,volume 56))

Abstract

The ubiquitous presence of heterocyclic moieties in everyday life justifies the ongoing intensive research within the synthetic community to discover effective methodologies for their construction. As the social concern regarding environmental protection gains importance, the use of light as the ultimate green promoter for chemical reactions has been revived in the scientific community. Specifically, visible-light photoredox processes based on metal- and organic photosensitizer are attracting significant attention and have seen an exceptional advance recently.

Additionally, continuous-flow processing has enabled a safer and more efficient generation of various heterocycles, whilst allowing their syntheses in a scalable manner. In this chapter, recent achievements in the area of continuous-flow aided photoredox synthesis are covered, including some general remarks on instrumentation, theoretical background and selected flow UV-photochemistry examples.

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Abbreviations

Cu(Xantphos)(dmp)BF4 :

Copper (I) (2,9-dimethyl-1,10-phenanthroline-kN1,kN10)[1,1′-(9,9-dimethyl-9H-xanthene-4,5-diyl)bis[1,1-diphenylphosphine-kP]](T-4) tetrafluoroborate

DIY:

Do it yourself

DMAP:

N,N-dimethylaminopyridine

fac-Ir(ppy)3 :

fac-Tris(2-phenylpyridine)iridium (III)

Fe(phen)3(NTf2)2 :

Iron (II) tris(1,10-phenanthroline-kN1,kN10)-(OC-6-11) di(1,1,1-trifluoro-N-[(trifluoromethyl)sulfonyl]methanesulfonamide)

Ir(dF(CF3)ppy)2(dtbbpy)PF6 :

[4,4′-Bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis[3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]Iridium(III) hexafluorophosphate

[Ir(dtbbpy)(ppy)2]PF6 :

4,4′-Bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis[2-(2-pyridinyl-N)phenyl-C]iridium(III) hexafluorophosphate

LEDs:

Light-emitting diodes

N-Boc:

N-tert-Butyloxycarbonyl

Ru(bpy)3(PF6)2 :

Tris(2,2′-bipyridine)ruthenium(II) hexafluorophosphate

Ru(bpy)3Cl2 :

Tris(bipyridyl)ruthenium(II) dichloride

tert-BuOOH:

tert-Butyl hydroperoxide

TMSCN:

Trimethylsilyl cyanide

TrocN3 :

2,2,2-Trichloroethyl azidoformate

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Authors and Affiliations

  1. Institute of Chemistry, University of Graz, Graz, Austria

    Toma Glasnov

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  1. Toma Glasnov
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Correspondence to Toma Glasnov .

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Editors and Affiliations

  1. Department of Chemistry, University of Leuven (KU Leuven), Leuven, Belgium

    Upendra K. Sharma

  2. Department of Chemistry, University of Leuven (KU Leuven), Leuven, Belgium

    Erik V. Van der Eycken

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Glasnov, T. (2018). Photochemical Synthesis of Heterocycles: Merging Flow Processing and Metal-Catalyzed Visible Light Photoredox Transformations. In: Sharma, U., Van der Eycken, E. (eds) Flow Chemistry for the Synthesis of Heterocycles. Topics in Heterocyclic Chemistry, vol 56. Springer, Cham. https://doi.org/10.1007/7081_2018_20

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