A methodology for the photocatalyzed radical trifluoromethylation of indoles: A combined experimental and computational study

Shelli A. Miller, Bas van Beek, Trevor A. Hamlin*, F. Matthias Bickelhaupt, Nicholas E. Leadbeater

*Corresponding author for this work

Research output: Contribution to JournalArticleAcademicpeer-review

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Abstract

A methodology for the direct introduction of the trifluoromethyl group on to indole scaffolds is presented. The procedure involves the use of sodium trifluoromethylsulfinate (Langlois reagent) as the source of the trifluoromethyl radical, and is performed photochemically with 2-tert-butylanthraquinone as a photocatalyst. The reaction has also been probed computationally. Reaction kinetics and molecular orbital analyses from our quantum chemical computations successfully predict and rationalize the formation of the experimentally observed product and, in the case of 1-methylbenzimidazole, even reproduce the same qualitative trends in regioisomer preference.

Original languageEnglish
Pages (from-to)94-100
Number of pages7
JournalJournal of Fluorine Chemistry
Volume214
Early online date11 Aug 2018
DOIs
Publication statusPublished - Oct 2018

Funding

This work was supported financially by the University of Connecticut . Additionally, we thank the Netherlands Organization for Scientific Research (NWO) for financial support through the Planetary and Exo-Planetary Science program (PEPSci) and the Dutch Astrochemistry Network (DAN). We would also like to thank undergraduate students Joshua Paolillo and Madeline Williams (University of Connecticut) for contributions to the experimental components of this project. Appendix A

FundersFunder number
Dutch Astrochemistry Network
Planetary and Exo-Planetary Science program
University of Connecticut
Nederlandse Organisatie voor Wetenschappelijk Onderzoek

    Keywords

    • Density functional calculations
    • Indoles
    • Langlois reagent
    • Photocatalysis
    • Trifluoromethylation

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