Fluorosulfonylvinylation of Unactivated C(sp<sup>3</sup>)–H via Electron Donor–Acceptor Photoactivation
Xueyan Zhao, Dengfeng Chen, Shengzhen Zhu, Jinyue Luo, Saihu Liao, Binnan Zheng, Shenlin Huang
Abstract
An electron donor–acceptor (EDA) complex photoactivation strategy for radical fluorosulfonylation is disclosed for the first time. Simply upon blue light irradiation, the FSO 2 radical can be generated efficiently under catalyst-free, base-free, and additive-free conditions, which enables facile access to 6-keto alkenylsulfonyl fluorides from readily available propargyl alcohols and FSO 2 Cl. The 6-keto alkenylsulfonyl fluoride motif has been showcased as a versatile SuFEx hub with diverse follow-up derivatizations.
Topics & Concepts
ChemistryPropargylAcceptorCatalysisFluorideElectron acceptorPhotochemistryElectron donorCombinatorial chemistryIrradiationOrganic chemistryInorganic chemistryPhysicsCondensed matter physicsNuclear physicsFluorine in Organic ChemistrySulfur-Based Synthesis TechniquesRadical Photochemical Reactions