Sulfur Assisted Tandem Electrophilic Fluorinative Deacylation: Synthesis of α‑Fluoro β‑Ketosulfides

A successful synthesis of α-fluoro-β-ketosulfides using an electrophilic fluorination method has been reported for the first time. The reaction proceeds via an electrophilic fluorination of α-sulfenyl-β-diketones followed by an unexpected tandem deacylation. The resulting products, α-fluoro-β-ketosu...

Full description

Saved in:
Bibliographic Details
Published in:Journal of organic chemistry 2017-09, Vol.82 (18), p.9525-9536
Main Authors: Varun, Begur Vasanthkumar, Prabhu, Kandikere Ramaiah
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:A successful synthesis of α-fluoro-β-ketosulfides using an electrophilic fluorination method has been reported for the first time. The reaction proceeds via an electrophilic fluorination of α-sulfenyl-β-diketones followed by an unexpected tandem deacylation. The resulting products, α-fluoro-β-ketosulfides, are easily oxidized to the corresponding α-fluoro-β-ketosulfones, which can be used for further useful olefination reactions.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.7b01547