Work

Synthesis of Polycyclic Oxazolinium Compounds from Aryloxazolines and Alkynes via Dual Photoredox/Gold Catalysis and Rhodium Catalysis

Year: 2025

Type: article

Abstract: A series of polycyclic oxazolinium compounds is synthesized from various aryloxazolines with silyl‐substituted alkynes and internal alkynes via two synthetic pathways. By using dual photoredox/gold catalysis, the coupling of 2‐aryloxazoline diazonium compounds with silyl‐substituted alkynes affords silyl‐substituted polycyclic oxazoliniums in 20%–36% yield. The coupling of 2‐aryloxazolines with internal alkynes affords polycyclic oxazoliniums with up to 81% yield by Rh‐catalyzed CH bond functionalization. X‐ray crystallographic analysis and circular dichroism reveal the successful coupling of chiral (R)‐2‐aryloxazolines with internal alkynes and affording the corresponding chiral (R)‐oxazoliniums. Cytotoxicity analysis of the polycyclic oxazolinium compounds reveals cytotoxic activity on cancerous HeLa cells in micromolar dosage, with the lowest IC50 of 6.4 μM.

Source: Advanced Synthesis & Catalysis

DOI: 10.1002/adsc.70023