Aromatic iodonium/sulfonium rearrangement using difluoroenol silyl ethers

Abstract

Difluoroenol silyl ethers are a unique class of enol silyl ethers that are widely used as a powerful difluoroalkylating reagent to incorporate difluoromethylene groups into organic molecules. In this context, we revealed a fluorine effect that the difluoroenol silyl ethers exhibit the oxygen nucleophilicity in lieu of traditional α-carbon nucleophilicity toward the aromatic iodonium/sulfonium species, thus allowing us to develop difluoroalkylative [3,3]-rearrangement of aryl iodanes and aryl sulfoxides and the difluoroalkylative dearomatization of aryl sulfoxides. In this article, we summarize these works and illustrate the logic of our design.

GRAPHICAL ABSTRACT

Keywords:

• Rearrangement
• dearomatization
• hypervalent iodine chemistry
• sulfur chemistry

Correction Statement

This article has been corrected with minor changes. These changes do not impact the academic content of the article.

Additional information

Funding

This work was supported by National Natural Science Foundation of China (NSFC-21901232).