Cobalt- or copper-catalyzed synthesis of gem-difluoroallyl MIDA boronates from α-trifluoromethyl alkenes

[Display omitted] •MIDA boronates are versatile building blocks for organic synthesis.•The functionalized gem-difluoroalkenes are valuable synthetic intermediates.•Co- or Cu-catalyzed borylation of α-trifluoromethyl alkenes.•Synthesis of gem-difluoroallyl MIDA boronates. A novel two-step synthesis o...

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Veröffentlicht in:Tetrahedron letters 2020-06, Vol.61 (23), p.151940, Article 151940
Hauptverfasser: Liu, Yisen, Li, Chunmei, Liu, Chuan, He, Jingjing, Zhao, Xianghu, Cao, Song
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Sprache:eng
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Zusammenfassung:[Display omitted] •MIDA boronates are versatile building blocks for organic synthesis.•The functionalized gem-difluoroalkenes are valuable synthetic intermediates.•Co- or Cu-catalyzed borylation of α-trifluoromethyl alkenes.•Synthesis of gem-difluoroallyl MIDA boronates. A novel two-step synthesis of gem-difluoroallyl MIDA boronates, which are air- and moisture-stable fluorine-containing building blocks for potential applications in iterative cross-couplings, was developed. The first step involves cobalt- or copper-catalyzed defluoroborylation of α-trifluoromethyl alkenes with B2pin2 in the absence of ligand. Next, without further purification, the resulting gem-difluroallylboronic acid pinacol ester was converted to gem-difluoroallyl MIDA boronates by heating in the presence of MIDA.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2020.151940