FeF3‐Promoted Radical Fluoroalkylation of o‐Alkenylaryl Isocyanides to Access 2‐Fluoroalkylated Quinolines

An iron(III)‐promoted radical fluoroalkylation of o‐alkenylaryl isocyanides has been developed using readily available perfluoroalkyl iodides as fluoroalkyl source. This cyclization reaction features broad substrate scope and provides a simple and efficient approach for regioselective construction o...

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Veröffentlicht in:European journal of organic chemistry 2024-08, Vol.27 (30), p.n/a
Hauptverfasser: Zhou, Xin‐Yin, Zhang, Wei‐Ming, Lu, Cheng‐Wei, Wang, Hua‐Hua, Zhang, Xiao‐Hong, Zhang, Xing‐Guo, Tu, Hai‐Yong
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Sprache:eng
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Zusammenfassung:An iron(III)‐promoted radical fluoroalkylation of o‐alkenylaryl isocyanides has been developed using readily available perfluoroalkyl iodides as fluoroalkyl source. This cyclization reaction features broad substrate scope and provides a simple and efficient approach for regioselective construction of biologically important 2‐fluoroalkylated quinolines in 38–81 % yields. An efficient method for preparing quinolines through iron(III)‐promoted radical fluoroalkylation was developed. In the presence of FeF3 and Cs2CO3, a variety of o‐alkenylaryl isocyanides smoothly underwent the radical fluoroalkylation with perfluoroalkyl iodides to afford biologically important 2‐fluoroalkylated quinolines in 38–81 % yields. Moreover, the conditions are compatible with nonfluorinated alkyl iodides leading to 2‐alkylated quinolines.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202400434