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Synthesis of Indolophanes by Photochemical Macrocyclization

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2016

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Pfaffenbach, Magnus
Roller, Alexander

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https://doi.org/10.1002/chem.201600835
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Chemistry - A European Journal. 2016, 22(25), pp. 8444-8447. ISSN 0947-6539. eISSN 1521-3765. Available under: doi: 10.1002/chem.201600835

Zusammenfassung

Herein, we report the synthetically practical, short, and general access to novel indolophane architectures by means of a photochemical C-H activation process-the Witkop cyclization. These highly strained scaffolds were obtained by photoinduced ring closure and feature atropisomerism as well as aromatic ring current effects, which both have been investigated. The prevailing regioselectivity of theWitkop cyclization reaction was completely reversed by the presence of a quaternary carbon center, exerting a strong Thorpe-Ingold effect on the system for which experimental-evidence is provided.

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540 Chemie

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ISO 690PFAFFENBACH, Magnus, Alexander ROLLER, Tanja GAICH, 2016. Synthesis of Indolophanes by Photochemical Macrocyclization. In: Chemistry - A European Journal. 2016, 22(25), pp. 8444-8447. ISSN 0947-6539. eISSN 1521-3765. Available under: doi: 10.1002/chem.201600835
BibTex
@article{Pfaffenbach2016Synth-35521,
  year={2016},
  doi={10.1002/chem.201600835},
  title={Synthesis of Indolophanes by Photochemical Macrocyclization},
  number={25},
  volume={22},
  issn={0947-6539},
  journal={Chemistry - A European Journal},
  pages={8444--8447},
  author={Pfaffenbach, Magnus and Roller, Alexander and Gaich, Tanja}
}
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