Calcium Carbide as a Surrogate of Acetylene: Copper‐Catalyzed Construction of 3‐Methylene‐2‐arylisoindolin‐1‐ones

An efficient method for the synthesis of 3‐methylene‐2‐arylisoindolin‐1‐ones through Sonogashira cross‐coupling/nucleophilic addition tandem reactions using calcium carbide as an alkyne source, 2‐bromo‐N‐arylbenzamides as starting materials and copper as a catalyst is described. The significant adva...

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Veröffentlicht in:Asian journal of organic chemistry 2022-07, Vol.11 (7), p.n/a
Hauptverfasser: Liu, Haiyan, You, Xinjie, Wen, Fei, Zhang, Zeshuai, Li, Zheng
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Sprache:eng
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Zusammenfassung:An efficient method for the synthesis of 3‐methylene‐2‐arylisoindolin‐1‐ones through Sonogashira cross‐coupling/nucleophilic addition tandem reactions using calcium carbide as an alkyne source, 2‐bromo‐N‐arylbenzamides as starting materials and copper as a catalyst is described. The significant advantages of this strategy include the use of cheap and easy‐to‐handle solid alkyne source as a surrogate of inflammable and explosive gaseous acetylene, inexpensive catalyst, wide scope of substrates, simple manipulations, and simple work‐up procedures. Calcium carbide as a surrogate of acetylene was used to construct N‐heterocycles in the presence of a copper catalyst. The cheap, safe, and easy‐to‐operate properties of calcium carbide compared with inflammable, explosive, and difficult‐to‐handle acetylene render the reactions easier to apply to various important synthesis.
ISSN:2193-5807
2193-5815
DOI:10.1002/ajoc.202200204