α-Amination at BODIPY and BOPHY Core via Metal-Free Regiospecific Cross Dehydrogenative Coupling Reaction Toward the Development of Lysotracker

Kartik Dutta; Richa Agrawal; Nitish Chauhan; Bhaskar Das; Amey P Wadawale; Mahesh Subramanian; Soumyaditya Mula

doi:10.1021/acs.orglett.5c02190

α-Amination at BODIPY and BOPHY Core via Metal-Free Regiospecific Cross Dehydrogenative Coupling Reaction Toward the Development of Lysotracker

Org Lett. 2025 Jul 1. doi: 10.1021/acs.orglett.5c02190. Online ahead of print.

Authors

Kartik Dutta¹, Richa Agrawal^{1

2}, Nitish Chauhan^{1

2}, Bhaskar Das¹, Amey P Wadawale³, Mahesh Subramanian^{1

2}, Soumyaditya Mula^{1

2}

Affiliations

¹ Bio-Organic Division, Bhabha Atomic Research Centre, Mumbai 400085, India.
² Homi Bhabha National Institute, Anushakti Nagar, Mumbai 400094, India.
³ Chemistry Division, Bhabha Atomic Research Centre, Mumbai 400085, India.

PMID: 40590171
DOI: 10.1021/acs.orglett.5c02190

Abstract

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(sp²)-N(sp³) 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 3t, showed an excellent lysosome targeting ability with turn-on fluorescence inside the lysosome, making it an efficient Lysotracker agent.