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 language | English |
|---|---|
| Pages (from-to) | 94-100 |
| Number of pages | 7 |
| Journal | Journal of Fluorine Chemistry |
| Volume | 214 |
| Early online date | 11 Aug 2018 |
| DOIs | |
| Publication status | Published - 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
| Funders | Funder 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
