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Updated: Jan 9, 2026
Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
Published on: February 24, 2015
Redox-Neutral Radical Annulation of Challenging Alkynes with Aryl Sulfoxonium Ylides for 1-Naphthol Synthesis
Hongyin Huang1, Yilian Lu1, Mengqi Gui1
1Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources (Ministry of Education of China), Guangxi Key Laboratory of Chemistry and Molecular Engineering of Medicinal Resources, University Engineering Research Center for Chemistry of Characteristic Medicinal Resources (Guangxi), School of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, Guilin 541004, China.
Abstract:
This radical strategy represents the first use of sulfoxonium ylide-derived radicals in 1-naphthol synthesis and overcomes the substrate limitations of classical carbene-based methods. It enables annulation of unactivated terminal alkynes─previously challenging substrates─under mild, metal- and additive-free, visible-light conditions. Mechanistic studies support formation of a highly electrophilic hindered radical cation that undergoes polarity-inverted addition and benzannulation, establishing sulfoxonium ylides as versatile radical precursors for modular 1-naphthol construction.
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