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Issue 41, 2020
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Synthesis of difluoroalkylated 2-azaspiro[4.5]decane derivatives via copper-catalyzed difluoroalkylation/dearomatization of N-benzylacrylamides

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Abstract

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.

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

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Article information


Submitted
05 Sep 2020
Accepted
12 Oct 2020
First published
12 Oct 2020

Org. Biomol. Chem., 2020,18, 8376-8380
Article type
Communication

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

C. Li, Y. Zhao, J. Zhou, X. Wang, J. Hou, Y. Song, W. Liu and G. Han, Org. Biomol. Chem., 2020, 18, 8376
DOI: 10.1039/D0OB01833C

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