Synthesis of difluoroalkylated 2-azaspiro[4.5]decane derivatives copper-catalyzed difluoroalkylation/dearomatization of -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 additio...

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Published inOrganic & biomolecular chemistry Vol. 18; no. 41; pp. 8376 - 838
Main Authors Li, Chengwen, Zhao, Yilin, Zhou, Jiaxin, Wang, Xue, Hou, Jingli, Song, Yuguang, Liu, Wenjuan, Han, Guifang
Format Journal Article
LanguageEnglish
Published 28.10.2020
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Summary: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. A copper-catalyzed synthesis of difluoroalkylated spiro-azacycles from N -benzylacrylamides is presented. The reaction involves the β-difluoroalkylation of acrylamide, 5- exo cyclization, and dearomatization.
Bibliography:10.1039/d0ob01833c
Electronic supplementary information (ESI) available. See DOI
ISSN:1477-0520
1477-0539
DOI:10.1039/d0ob01833c