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Updated: Oct 16, 2026

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Difunctionalization of unsaturated hydrocarbons via EDA complexes to access pentafluorosulfanyl thioethers
Xiaofeng Zhang1, Yuanyang Jiang1, Hui-Yi Yang1
1Institute of Green Chemistry and Environment, College of Chemistry and Chemical Engineering, Inner Mongolia University, Hohhot, 010021, P. R. China.
Abstract:
Recently, the pentafluorosulfanyl (SF5) group has attracted considerable interest from medicinal chemists owing to its capacity to significantly enhance the pharmaceutical properties of small-molecule drug candidates. However, a general method for three-component pentafluorosulfanylation of electron-deficient alkenes remains elusive. Herein, we present an electron donor-acceptor (EDA) complex photoactivation strategy for the thiopentafluorosulfanylation of unsaturated hydrocarbons, including electron-deficient alkenes, alkynes, 1,6-enynes, and even acetylene gas. The utility of this approach is demonstrated through the synthesis of a diverse array of pentafluorosulfanyl thioethers and the late-stage functionalization of complex molecules, including pharmaceuticals, natural products, and amino acid derivatives. This work establishes a framework for designing atom-economical difunctionalization reactions that employ green LEDs under mild conditions. Moreover, mechanistic studies support an EDA complex-mediated pathway and identify ArSCl as a key intermediate formed upon generation of the thiyl radical.
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