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 |
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Format: | Artikel |
Sprache: | eng |
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•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. |
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ISSN: | 0040-4039 1873-3581 |
DOI: | 10.1016/j.tetlet.2020.151940 |