Visible-light-induced tandem difluoroalkylated spirocyclization of N -arylpropiolamides: access to C3-difluoroacetylated spiro[4,5]trienones

A visible-light-catalyzed difluoroacetylated spirocyclization of N -arylpropiolamides with ethyl bromodifluoroacetate as a CF 2 CO 2 Et radical precursor is described. This approach allows the formation of two carbon–carbon bonds and one carbon–oxygen bond in a single reaction through a sequence of...

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Veröffentlicht in:New journal of chemistry 2022-02, Vol.46 (9), p.4470-4482
Hauptverfasser: Yuan, Jin-Wei, Shen, Lu, Ma, Meng-Yao, Feng, Shi, Yang, Wan, Yang, Liang-Ru, Xiao, Yong-Mei, Zhang, Shou-Ren, Qu, Ling-Bo
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Sprache:eng
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Zusammenfassung:A visible-light-catalyzed difluoroacetylated spirocyclization of N -arylpropiolamides with ethyl bromodifluoroacetate as a CF 2 CO 2 Et radical precursor is described. This approach allows the formation of two carbon–carbon bonds and one carbon–oxygen bond in a single reaction through a sequence of C–H oxidative coupling, ipso -cyclization and dearomatization processes. This protocol affords a straightforward route to synthesize CF 2 CO 2 Et-containing spiro[4.5]trienones in moderate to good yields.
ISSN:1144-0546
1369-9261
DOI:10.1039/D2NJ00131D