Radical Ring-Opening Fluorosulfonylation of Methylenecyclobutanols via Electron Donor–Acceptor Photoactivation

A visible-light-mediated catalyst- and additive-free method for radical ring-opening fluorosulfonylation of methylenecyclobutanols is reported. Sulfuryl chlorofluoride acts as a FSO2 radical precursor as well as an electron acceptor to form electron donor–acceptor complexes with various methylenecyclobutanol substrates. This method shows fully regioselective and (E)-stereoselective ring-opening processes, providing a variety of FSO2-functionalized γ,δ-unsaturated carbonyls in 38–77% yields. A selection of product diversifications has been studied to demonstrate the versatility of these sulfonyl fluoride products.