Preparation of Unsymmetrical Disulfides via Catalytic Lewis Base Activation of N -(Organodithio)phthalimides
Abstract
High Resolution Image Download MS PowerPoint Slide N -(Organodithio)phthalimides have attracted significant attention as versatile disulfide transfer reagents, but their applications have been largely limited to substitution reactions with highly reactive nucleophiles. We report a Lewis base–catalyzed activation strategy that expands the scope of N -(organodithio)phthalimides to the bifunctionalization of less reactive olefins. Nucleophile-tethered olefins undergo smooth cyclization to furnish heterocycle-appended disulfides. With broad substrate scope and the ready availability of N -(organodithio)phthalimides from bilateral reagents, this strategy enables modular construction of unsymmetrical disulfides.
Fields of Study & Subjects
Sulfur-Based Synthesis Techniques
Synthesis and Reactivity of Sulfur-Containing Compounds
Catalytic C–H Functionalization Methods
Publication details
- Journal / source
- The Journal of Organic Chemistry
- Publisher
- American Chemical Society (ACS)
- Volume
- 91
- Issue
- 4
- Pages
- 1817–1822
- Publication date
- 19 January 2026
- Language
- EN