Structurally Diverse Nitrogen-Rich Scaffolds via Continuous Photo-Click Reactions
Continuous flow technology was exploited for the effective generation of nitrile imines via photolysis of substituted aryl tetrazoles. The resulting photo-click process rapidly affords advanced nitrogen-rich scaffolds upon the subsequent trapping of the reactive dipole with alkenes, alkynes, and benzylic amines. Crucially, this approach uncovers the differential reactivity for ether vs amine tethers, thus providing facile and scalable access to underexplored medicinally relevant heterocyclic entities.
Authors
- Julia Bruno-Colmenárez (ORCID: https://orcid.org/0000-0001-9476-7189)
- Brendan Twamley
- Megan Smyth (ORCID: https://orcid.org/0000-0002-2771-0382)
- Thomas S. Moody (ORCID: https://orcid.org/0000-0002-8266-0269)
- Scott Wharry (ORCID: https://orcid.org/0000-0003-4857-4866)
- Marcus Baumann (ORCID: https://orcid.org/0000-0002-6996-5893)
- Davin Cronly (ORCID: https://orcid.org/0000-0002-7708-7672)
Institutions
- University College Dublin (IE)
- Trinity College Dublin (IE)
- Almac (United Kingdom) (GB)
Publication Details
- Journal
- Organic Letters
- Published
- 2024-11-26
- DOI
- https://doi.org/10.1021/acs.orglett.4c03953
- Citations
- 7
- Primary Topic
- Click Chemistry and Applications
- Type
- article
- Field-Weighted Citation Impact
- 1.75
Funders
- Science Foundation Ireland
- University College Dublin
- Irish Research Council