Palladium-Catalyzed Cyclization/Sulfonylation Enabling Access to 2-Pyrrolidinone-Functionalized Allylic Sulfones
Abstract
An efficient Pd-catalyzed cyclization/sulfonylation reaction of N -allylbromoacetamides with Na 2 S 2 O 4 and allyl esters via “SO 2 ” insertion has been developed, enabling the first synthesis of 2-pyrrolidinone-functionalized allylic sulfones. In this protocol, inexpensive and readily available Na 2 S 2 O 4 functions dually as a sulfur dioxide source and a single-electron donor, thereby sustaining the catalytic cycle. The reaction exhibits a broad substrate scope and excellent tolerance to diverse functional groups, affording a wide range of allylic sulfones with exclusive ( E ) selectivity. Mechanistic studies suggest a reaction pathway involving intramolecular radical cyclization, the insertion of “SO 2,” and subsequent allylic substitution of a π-allyl-Pd(II) intermediate in a single reaction.
Fields of Study & Subjects
Sulfur-Based Synthesis Techniques
Catalytic C–H Functionalization Methods
Catalytic Cross-Coupling Reactions
Publication details
- Journal / source
- The Journal of Organic Chemistry
- Publisher
- American Chemical Society (ACS)
- Volume
- 91
- Issue
- 8
- Pages
- 3354–3362
- Publication date
- 11 February 2026
- Language
- EN