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

IF 4 2区化学 Q2 CHEMISTRY, APPLIED

Advanced Synthesis & Catalysis Pub Date : 2025-08-21 DOI:10.1002/adsc.70023

Lai-Yi Tsang, Ajcharapan Tantipanjaporn, Karen Ka-Yan Kung, Hoi-Yi Sit, Wa-Yi O, Aries Kwok-Heung Chan, Nathanael Chun-Him Lai, Man-Kin Wong

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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.

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芳杂唑啉和炔基双光氧化还原/金催化和铑催化合成多环恶唑啉化合物

以不同的芳基恶唑啉为原料，通过硅基取代炔和内炔两种合成途径合成了一系列多环恶唑啉化合物。通过双光氧化还原/金催化，2 -芳基恶唑啉重氮化合物与硅基取代炔偶联得到硅基取代多环恶唑，产率为20% ~ 36%。2 -芳基恶唑啉与内炔的偶联通过Rh催化的C - H键功能化得到了产率高达81%的多环恶唑。X射线晶体分析和圆二色性显示手性(R)‐2‐芳基恶唑啉与内炔成功偶联，并得到相应的手性(R)‐恶唑啉。对多环恶唑啉类化合物的细胞毒性分析表明，在微摩尔剂量下，其对癌变HeLa细胞具有细胞毒活性，IC50最低为6.4 μM。

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来源期刊

Advanced Synthesis & Catalysis 化学-应用化学

CiteScore

9.40

自引率

7.40%

发文量

447

审稿时长

1.8 months

期刊介绍： Advanced Synthesis & Catalysis (ASC) is the leading primary journal in organic, organometallic, and applied chemistry. The high impact of ASC can be attributed to the unique focus of the journal, which publishes exciting new results from academic and industrial labs on efficient, practical, and environmentally friendly organic synthesis. While homogeneous, heterogeneous, organic, and enzyme catalysis are key technologies to achieve green synthesis, significant contributions to the same goal by synthesis design, reaction techniques, flow chemistry, and continuous processing, multiphase catalysis, green solvents, catalyst immobilization, and recycling, separation science, and process development are also featured in ASC. The Aims and Scope can be found in the Notice to Authors or on the first page of the table of contents in every issue.