Organophotocatalyzed Alkyl/Arylsulfonylation of Vinylcyclopropanes

Allyl sulfones are an essential pharmacophore in many bioactive compounds. To combat their synthetic barrier, we report a practical, straightforward organophotocatalyzed methodology for accessing miscellaneously functionalized allyl sulfone derivatives using inexpensive and bench-stable sodium sulfinate salts under mild conditions. This photo-catalyzed radical sulfonylation provides access to a variety of allyl sulfones in good to excellent yields with high E : Z selectivity. A wide range of vinyl cyclopropanes, as well as aryl/hetero and alkyl sodium sulfinates, were tolerated and reliable in gram-scale synthesis. Later on, further functionalization of allyl sulfones was demonstrated. A plausible mechanism for radical sulfonylation is proposed from the control experiments.