Reactions of Tröger’s Base Derivatives with Aryne Intermediates
Abstract
Reaction of rac -Tröger’s base (TB) with aryl halides is described via ring opening with concomitant N -arylation in the presence of the t -BuOK/DMSO reagent system. The methylene bridge of the Tröger’s base derivatives is eliminated by an aryne intermediate formed in situ, leading to the generation of N -arylated product in up to 67% yield. The reaction scope has also been extended to synthesize an enantiopure compound involving the rearrangement of the methylene bridge.
Fields of Study & Subjects
Molecular spectroscopy and chirality
Cyclization and Aryne Chemistry
Natural Compound Pharmacology Studies
Publication details
- Journal / source
- The Journal of Organic Chemistry
- Publisher
- American Chemical Society (ACS)
- Volume
- 91
- Issue
- 7
- Pages
- 3017–3024
- Publication date
- 6 February 2026
- Language
- EN