Visible-Light-Driven C-3 Selenocyanation of Indoles with Elemental Selenium and TMSCN
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<i>H</i>-pyrimido[1,2-<i>a</i>]azepin-5-ium selenocyanate is generated in situ from DBU, elemental selenium, and TMSCN.
Authors
- Qinghong Li (ORCID: https://orcid.org/0009-0001-1179-2758)
- Yong‐Liang Ban (ORCID: https://orcid.org/0000-0003-4028-3503)
- Wei‐Wu Song
- Tao Huang (ORCID: https://orcid.org/0000-0003-1609-9642)
- Xue Liu (ORCID: https://orcid.org/0000-0002-9723-4393)
- Qiang Liu (ORCID: https://orcid.org/0000-0001-8845-1874)
- Xiaobing Liu (ORCID: https://orcid.org/0000-0002-0680-1947)
- Like Wang (ORCID: https://orcid.org/0009-0002-0952-6204)
- Ran Chen (ORCID: https://orcid.org/0009-0007-9121-9647)
Institutions
- Zhoukou Normal University (CN)
- Institute of Plant Genetics, Polish Academy of Sciences (PL)
- Lanzhou University (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-09-01
- DOI
- https://doi.org/10.1021/acs.orglett.5c03266
- Citations
- 3
- Primary Topic
- Sulfur-Based Synthesis Techniques
- Type
- article
- Field-Weighted Citation Impact
- 2.81
Funders
- Zhoukou Normal University
- Natural Science Foundation of Henan Province
- Science and Technology Department of Henan Province
- National College Students Innovation and Entrepreneurship Training Program