An efficient method for the synthesis of alkyl α,α-difluorosulfonates has been developed. The selection of the 2-pyridyl group as the aryl substitute on the sulfone is critically important for the success of this transformation (see scheme). The synthetic application of fluorinated sulfones is extended and a unique solution is provided for a long-standing challenge in nucleophilic difluoro(sulfonato)methylation reactions. Detailed facts of importance to specialist readers are published as "Supporting Information". Such documents are peer-reviewed, but not copy-edited or typeset. They are made available as submitted by the authors. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.