銅催化碳-氮偶合反應:吲哚酮的合成應用

Cooper-Catalyzed C-N cross-coupling reaction: the application for the synthesis of oxindoles

康庭維(Ting-Wei Kang)

指導教授 ： 謝仁傑

淡江大學/理學院/化學學系碩士班/碩士(2013年)

https://doi.org/10.6846/TKU.2013.00778

摘要

第一部分:
利用高效率且符合經濟效益的串聯反應在碘化亞銅催化不同取代基的鄰溴苯乙腈進行形成高產率及具有許取代基的3,3 spiro-oxindole結構的產物，其可以在短步驟中合成天然物coerulescine。
第二部份:
利用高效銅催化分子內形成碳-氮鍵，利用起始物鄰溴苯乙醯胺在少量的氧化亞銅和鄰苯二胺空氣中可合成具有高產率的3,3 spiro-oxindole衍生物結構。

關鍵字

烏爾曼反應 ； 螺－吲哚酮 ； 串聯反應

並列摘要

The 1st Part:
An efficient and novel procedure for the copper catalyzed domino coupling reaction has been developed, which afforded various oxindoles in good to excellent yields with tolerance of various substituents. In addition, this method could be applied to synthesize coerulescine in short steps with high total yields.
The 2st Part:
An efficient copper-catalyzed intramolecular N-arylation was carried out by involving 2,2-substituted 2-(2-bromoaryl)acetamide to afford various substituted oxindoles with tiny loadings of Cu2O and benzene-1,2-diamine as catalytic system under aerobic conditions, which provided good to excellent yields with tolerance of wide variety of substrates.

並列關鍵字

Ullmann reaction ； spiro-oxindole ； domino reaction

參考文獻

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5.Ullmann, F.; Bieleeeki. Ber. Dtsch. Chem. Ges.1903, 36, 2382

6.Ullmann, F. Ber. Dtsch. Chem. Ges. 1904, 37, 853.

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