Synthesis of difluoroalkylated 2-azaspiro[4.5]decane derivatives via copper-catalyzed difluoroalkylation/dearomatization of N-benzylacrylamides

An efficient method for the synthesis of difluoroalkylated 2-azaspiro[4.5]decanes via copper-catalyzed difluoroalkylation of N-benzylacrylamides with ethyl bromodifluoroacetate has been established. The reaction experienced a tandem radical addition and dearomatizing cyclization process. In addition...

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Veröffentlicht in:Organic & biomolecular chemistry 2020-11, Vol.18 (41), p.8376-8380
Hauptverfasser: Li, Chengwen, Zhao, Yilin, Zhou, Jiaxin, Wang, Xue, Hou, Jingli, Song, Yuguang, Liu, Wenjuan, Han, Guifang
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Sprache:eng
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Zusammenfassung:An efficient method for the synthesis of difluoroalkylated 2-azaspiro[4.5]decanes via copper-catalyzed difluoroalkylation of N-benzylacrylamides with ethyl bromodifluoroacetate has been established. The reaction experienced a tandem radical addition and dearomatizing cyclization process. In addition, the resultant products can be smoothly converted into a difluoroalkylated quinolinone and saturated spirocyclohexanone scaffold.
ISSN:1477-0520
1477-0539
DOI:10.1039/d0ob01833c