Skeletal Transformation of Benzene Rings to Indoles via Arylthianthrenium Salts Strategy
Abstract
Herein, we describe a method employing an arylthianthrenium salts strategy for the direct skeletal transformation of the benzene rings commonly found in drugs into indoles via two consecutive site-selective C–H functionalizations. This method features a broad substrate scope and is applicable for the late-stage skeletal transformation of pharmaceuticals. For example, the insect growth regulator Pyriproxyfen, the antifungal agent Bifonazole, the nonsteroidal anti-inflammatory drug Flurbiprofen, and the natural product Salicin can all be rapidly transformed into the desired indole derivatives. As for the mechanistic studies, DFT calculations demonstrated that the nitrogen insertion proceeds through a reductive elimination involving an eight-membered ring intermediate, rather than a nitrene pathway.
Fields of Study & Subjects
Catalytic C–H Functionalization Methods
Quinazolinone synthesis and applications
Advanced Synthetic Organic Chemistry
Publication details
- Journal / source
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Volume
- 28
- Issue
- 5
- Pages
- 1790–1796
- Publication date
- 21 January 2026
- Language
- EN