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Visible-Light-Induced Cyclization/Aromatization of 2‑Vinyloxy Arylalkynes: Synthesis of Thio-Substituted Dibenzofuran Derivatives

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journal contribution
posted on 22.12.2020, 19:41 by Hui Chen, Yunyun Yan, Niuniu Zhang, Zuyu Mo, Yanli Xu, Yanyan Chen
A visible-light-induced cascade reaction of 2-vinyloxy arylalkynes with thiosulfonates was developed and provided unexpected thio-substituted dibenzofuran derivatives in moderate yields. Mechanistic studies revealed the thiosulfonylation product of 2-vinyloxy arylalkyne was the key intermediate, and the additive disulfide played the role of hydrogen abstraction in the aromatization process to offer the desired product. This reaction presents a new reaction mode for the construction of polycyclic oxygen heterocycles.