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- W3212052000 abstract "Modulating the reaction selectivity is highly attractive and pivotal to the rational design of synthetic regimes. The defluorinative functionalization of gem-difluorocyclopropanes constitutes a promising route to construct β-vinyl fluorine scaffolds, whereas chemo- and regioselective access to α-substitution patterns remains a formidable challenge. Presented herein is a robust Pd/NHC ligand synergistic strategy that could enable the C-F bond functionalization with exclusive α-regioselectivity with simple ketones. The key design adopted enolates as π-conjugated ambident nucleophiles that undergo inner-sphere 3,3'-reductive elimination warranted by the sterically hindered-yet-flexible Pd-PEPPSI complex. The excellent branched mono-defluorinative alkylation was achieved with a sterically highly demanding IHept ligand, while subtly less bulky SIPr acted as a bifunctional ligand that not only facilitated α-selective C(sp3)-F cleavage, but also rendered the newly-formed C(sp2)-F bond as the linchpin for subsequent C-O bond formation. These examples represented an unprecedented ligand-controlled regioselective and chemodivergent approach to various mono-fluorinated terminal alkenes and/or furans from the same readily available starting materials." @default.
- W3212052000 created "2021-11-22" @default.
- W3212052000 creator A5020469893 @default.
- W3212052000 creator A5032470395 @default.
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- W3212052000 creator A5052111964 @default.
- W3212052000 creator A5053030986 @default.
- W3212052000 creator A5073843322 @default.
- W3212052000 date "2021-01-01" @default.
- W3212052000 modified "2023-10-17" @default.
- W3212052000 title "Ligand-controlled regioselective and chemodivergent defluorinative functionalization of <i>gem</i>-difluorocyclopropanes with simple ketones" @default.
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- W3212052000 doi "https://doi.org/10.1039/d1sc05451a" @default.
- W3212052000 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/35003579" @default.
- W3212052000 hasPublicationYear "2021" @default.
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