Radical Ring-Opening Fluorosulfonylation of Methylenecyclobutanols via Electron Donor–Acceptor Photoactivation
Tianyu He, Chaoqiang Liang, Ping Jiang, Hui Liang, Saihu Liao, Shenlin Huang
Abstract
A visible-light-mediated catalyst- and additive-free method for radical ring-opening fluorosulfonylation of methylenecyclobutanols is reported. Sulfuryl chlorofluoride acts as a FSO 2 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 FSO 2 -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.
Topics & Concepts
ChemistryRing (chemistry)PhotochemistryAcceptorElectron acceptorCatalysisVisible spectrumElectronElectron donorOrganic chemistryOptoelectronicsPhysicsQuantum mechanicsCondensed matter physicsFluorine in Organic ChemistrySulfur-Based Synthesis TechniquesRadical Photochemical Reactions