A detailed study of irradiation requirements towards an efficient photochemical Wohl‐Ziegler procedure in flow

Holly E. Bonfield, Jason D. Williams, Wei Xiang Ooi, Stuart G. Leach, William J. Kerr, Lee J. Edwards

Research output: Contribution to journalArticle

Abstract

A platform has been developed to enable standardization of light sources, allowing consistent scale‐up from high‐throughput screening in batch to flow, using the same pseudo‐monochromatic light source. The impact of wavelength and light intensity on a photochemical reaction was evaluated within this platform using the Wohl‐Ziegler benzylic bromination of 4‐methyl‐3‐(trifluoromethyl)benzonitrile with N‐bromosuccinimide as a model system. It was found that only 40 % of the maximum light intensity was required while still maintaining reaction rate, allowing more reliable temperature control and lower energy consumption. The optimized reaction conditions were subsequently applied to a range of synthetically relevant (hetero)aromatic compounds under continuous conditions, exploring the scope of the process within a mild and scalable procedure.
LanguageEnglish
Pages938-944
Number of pages7
JournalChemPhotoChem
Volume2
Issue number10
Early online date5 Jun 2018
DOIs
Publication statusPublished - 31 Oct 2018

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Bromosuccinimide
Irradiation
Monochromators
Aromatic compounds
Photochemical reactions
Temperature control
Standardization
Reaction rates
Light sources
Screening
Energy utilization
Throughput
Wavelength
benzonitrile

Keywords

  • flow chemistry
  • halogenation
  • microreactors
  • photochemistry
  • reaction mechanisms

Cite this

Bonfield, Holly E. ; Williams, Jason D. ; Ooi, Wei Xiang ; Leach, Stuart G. ; Kerr, William J. ; Edwards, Lee J. / A detailed study of irradiation requirements towards an efficient photochemical Wohl‐Ziegler procedure in flow. In: ChemPhotoChem. 2018 ; Vol. 2, No. 10. pp. 938-944.
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A detailed study of irradiation requirements towards an efficient photochemical Wohl‐Ziegler procedure in flow. / Bonfield, Holly E.; Williams, Jason D.; Ooi, Wei Xiang; Leach, Stuart G.; Kerr, William J.; Edwards, Lee J.

In: ChemPhotoChem, Vol. 2, No. 10, 31.10.2018, p. 938-944.

Research output: Contribution to journalArticle

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