α-Amination at BODIPY and BOPHY Core via Metal-Free Regiospecific Cross Dehydrogenative Coupling Reaction Toward the Development of Lysotracker
We report a metal-free, efficient, and quick cross dehydrogenative coupling (CDC) methodology using phenyliodine(III) diacetate (PIDA) as an oxidant to synthesize regiospecific α-amino BODIPYs/BOPHYs via C(sp<sup>2</sup>)-N(sp<sup>3</sup>) bond formation. Twenty-seven coupled products were synthesized using different primary/secondary amines and commercial drug molecules. The regiospecificity and mechanism of the reactions were confirmed by NMR, EPR, HRMS, and X-ray crystallography studies. One of the synthesized molecules, BODIPY <b>3t</b>, showed an excellent lysosome targeting ability with turn-on fluorescence inside the lysosome, making it an efficient Lysotracker agent.
Authors
- Soumyaditya Mula (ORCID: https://orcid.org/0000-0001-5970-1184)
- Amey Wadawale
- Bhaskar Das
- Mahesh Subramanian
- Richa Agrawal
- Kartik Dutta
- Nitish Chauhan (ORCID: https://orcid.org/0000-0002-1449-297X)
Institutions
- Bhabha Atomic Research Centre (IN)
- Homi Bhabha National Institute (IN)
- Division of Chemistry (US)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-07-01
- DOI
- https://doi.org/10.1021/acs.orglett.5c02190
- Citations
- 1
- Primary Topic
- Luminescence and Fluorescent Materials
- Type
- article
- Field-Weighted Citation Impact
- 0.52
Funders
- Department of Atomic Energy, Government of India