Expanding the Potential of Heteroaryl Vinyl Sulfones

The easily available vinyl sulfone 3 showed great
potential for new applications in several fields such as organic synthesis
and bioconjugate formation. This was demonstrated by performing a
systematic assessment of its reactivity in Michael, radical, and cycloaddition
reactions. Heteroaryl vinyl sulfone 3 presented excellent
output in terms of reactivity and selectivity, proving superior to
phenyl vinyl sulfone 1 and with clear advantages over
bis-sulfone 2. This behavior might be due to the conformational
and orbital control exerted by the tetrazole unit according to DFT
calculations. Moreover, some alternative transformations to the Julia–Kocienski
olefination on the obtained products are also described.