Visible-Light [4+2] Homodimerization of Decomposition-Prone Styrenes via Electron Transfer Catalysis of Diaryl Diselenides.

Org Lett

Center for Metareceptome Research, Graduate School of Pharmaceutical Sciences, Chung-Ang University, 84 Heukseok-ro, Dongjak, Seoul 06974, Republic of Korea.

Published: May 2024

AI Article Synopsis

  • The study explores the use of diaryl diselenides as effective catalysts for the visible-light-driven [4+2] homodimerization of styrenes, which are typically unstable.
  • Only a small amount of TPTBF photocatalyst (0.5 mol %) and diaryl diselenides (1.5 mol %) were needed for this reaction to occur.
  • This process not only highlights the spontaneous electron transfer abilities of diaryl diselenides but also successfully converts various styrenes into tetralin derivatives using visible light.

Article Abstract

The facile electron transfer catalysis of diaryl diselenides was utilized for the visible-light [4+2] homodimerization of decomposition-prone styrenes. The reaction required only 0.5 mol % TPTBF photocatalyst and 1.5 mol % electron transfer catalyst (ArSe). The spontaneous electron transfer capability of diaryl diselenides was demonstrated for the first time, leading to the sequestration of redox-prone radical cation intermediates via electron transfer processes. A variety of polymerization-prone styrenes smoothly underwent the visible-light-promoted [4+2] homodimerization to tetralin derivatives.

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Source
http://dx.doi.org/10.1021/acs.orglett.4c01210DOI Listing

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