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Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
Published on: July 17, 2020
Visible-Light-Driven C-3 Selenocyanation of Indoles with Elemental Selenium and TMSCN
Yong-Liang Ban1, Xue Liu2, Tao Huang3
1School of Chemistry and Chemical Engineering, Zhoukou Normal University, Zhoukou 466001, China.
Abstract:
We develop a photocatalyst-free, visible-light-driven three-component reaction of indole, elemental selenium, and TMSCN in air at room temperature to synthesize indole 3-selenocyanoates. This protocol features eco-friendly, photocatalyst-free, elemental selenium, and TMSCN serves as the source of "SeCN". Notably, the gram-scale reaction and product derivatizations demonstrated the practicality and effectiveness of this synergistic protocol. Preliminary mechanistic investigations indicate that light-absorbing species 2,3,4,6,7,8,9,10-octahydro-1H-pyrimido[1,2-a]azepin-5-ium selenocyanate is generated in situ from DBU, elemental selenium, and TMSCN.
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