Visible-Light Driven Synthesis of Vinyl Amines without Photocatalyst
We developed a visible-light-induced vinyl amination of activated alkenes using TMSN<sub>3</sub> and CsF through EDA complex formation under an oxygen atmosphere. Without light, the EDA complex forms between activated alkene, CsF, and oxygen. Upon exposure to light, oxygen in the complex gets excited, initiating the HAT process. This method efficiently synthesizes vinyl-amine derivatives via a radical pathway, demonstrating good functional group tolerance and high yields in a short time. Further, the late-stage functionalization enables the synthesis of biologically active heterocycles.
Authors
- Devarajulu Sureshkumar (ORCID: https://orcid.org/0000-0002-6985-3496)
- Krishna Gopal Ghosh (ORCID: https://orcid.org/0000-0002-0336-7540)
- Debabrata Das (ORCID: https://orcid.org/0000-0002-5368-9150)
- Koustav Pal
Institutions
- Indian Institute of Science Education and Research Kolkata (IN)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2024-09-26
- DOI
- https://doi.org/10.1021/acs.joc.4c01624
- Citations
- 2
- Primary Topic
- Radical Photochemical Reactions
- Type
- article
- Field-Weighted Citation Impact
- 0.50
Funders
- Department of Science and Technology, Ministry of Science and Technology, India
- Council of Scientific and Industrial Research, India
- Indian Institute of Science Education and Research Kolkata
- Science and Engineering Research Board