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

  • Toma Glasnov
Chapter
Part of the Topics in Heterocyclic Chemistry book series (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.

Keywords

Continuous flow Flow reactor Heterocycles Light source Metal photosensitizers Organic photosensitizers Photoredox catalysis Visible and UV light 

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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© Springer International Publishing AG 2018

Authors and Affiliations

  1. 1.Institute of ChemistryUniversity of GrazGrazAustria

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