Triphenylphosphine-Mediated Bifunctional Activation to Unlock Electrochemical Deoxygenative Thiolation of Alcohols
Abstract
Herein, we report a metal-free electrochemical strategy for forming C–S bonds, which allowed us to obtain aryl, alkyl, allylic, and glycosyl thioethers using inexpensive alcohols as an electrophile and odorless disulfides as a sulfur source. The developed strategy fully eliminated the need for prefunctionalization of alcohols, thus showcasing a broad substrate scope, acceptable to excellent yields (52–93%), good functional group compatibility, and mild conditions. The key to the protocol is leveraging anodic oxidation, which drives PPh 3 to form alkoxyphosphonium intermediates, thereby activating the C–O bond of alcohols, while PPh 3 also reduces disulfides to generate RS – .
Fields of Study & Subjects
Sulfur-Based Synthesis Techniques
Radical Photochemical Reactions
Asymmetric Hydrogenation and Catalysis
Publication details
- Journal / source
- The Journal of Organic Chemistry
- Publisher
- American Chemical Society (ACS)
- Volume
- 91
- Issue
- 25
- Pages
- 8695–8703
- Publication date
- 15 June 2026
- Language
- EN