Visible-Light-Driven C-3 Selenocyanation of Indoles with Elemental Selenium and TMSCN.

Org Lett

State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, China.

Published: September 2025


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Article 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-1-pyrimido[1,2-]azepin-5-ium selenocyanate is generated in situ from DBU, elemental selenium, and TMSCN.

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http://dx.doi.org/10.1021/acs.orglett.5c03266DOI Listing

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