Single C(sp3)–F Bond Activation in a CF3 Group: Ipso-Defluorooxylation of (Trifluoromethyl)alkenes with Oximes

Single C(sp3)–F Bond Activation in a CF3 Group: Ipso-Defluorooxylation of (Trifluoromethyl)alkenes with Oximes

The first defluorinative ipso-functionalization reaction of (trifluoromethyl)­alkenes is reported. This exclusively regioselective ipso-defluorooxylation of (trifluoromethyl)­alkenes with oximes affords various attractive O-(1,1-difluoroallyl)­oxime ethers efficiently via a chemoselective single C­(...

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Veröffentlicht in:Organic letters 2019-02, Vol.21 (4), p.1130-1133
Hauptverfasser: Zeng, Hao, Zhu, Chuanle, Jiang, Huanfeng
Format: Artikel
Sprache:eng
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Zusammenfassung:The first defluorinative ipso-functionalization reaction of (trifluoromethyl)­alkenes is reported. This exclusively regioselective ipso-defluorooxylation of (trifluoromethyl)­alkenes with oximes affords various attractive O-(1,1-difluoroallyl)­oxime ethers efficiently via a chemoselective single C­(sp3)–F bond activation in the CF3 group. Primary mechanism studies indicated an anionic SN2-type substitution pathway might be involved in this transformation.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b00074