Skeletal Editing of Isoquinolines Via CN/CC Atom-Pair Swap Enables the Synthesis of 3-Arylthio-2-O-acylated Naphthols and DFT Studies
Abstract
A novel strategy for the synthesis of 3-substituted 2-O-acylated naphthols has been developed via a skeleton-editing approach. This transformation proceeds through a formal [4 + 2] cycloaddition between isoquinolinium salts and acyl chlorides, followed by thiazole extrusion. DFT calculations were employed to elucidate the reaction mechanism, supporting the proposed domino pathway. This method enables regioselective access to 3-substituted 2-O-acylated naphthols, which are difficult to obtain via conventional electrophilic substitution due to the inherent preference for C1 functionalization. Notably, unlike previous skeleton-editing reports that yield 1-substituted naphthalene, the present approach delivers products with a free C1 position, providing a valuable handle for further functionalization such as the construction of 1,1'-bi-2-naphthol derivatives.
Fields of Study & Subjects
Catalytic C–H Functionalization Methods
Radical Photochemical Reactions
Axial and Atropisomeric Chirality Synthesis
Publication details
- Journal / source
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Volume
- 28
- Issue
- 21
- Pages
- 6601–6606
- Publication date
- 18 May 2026
- Language
- EN