Fluorinated 1-phenyl-1H-tetrazol-5-yl sulfone derivatives as general reagents for fluoroalkylidene synthesis

The preparation of Julia-Kocienski olefination reagents 1-fluoropropyl, (cyclopropyl)fluoromethyl, 1-fluoro-2-methyl-2-propenyl, and 1-fluoro-5-hexenyl 1-phenyl-1H-tetrazol-5-yl (PT) sulfones via metalation followed by electrophilic fluorination is reported. Screening of olefination conditions showed that stereoselectivity which depended on reagent and carbonyl structure could be tuned either toward E- or Z-selectivity.