ol0c02281_si_001.pdf (4.48 MB)
anti-Hydroarylation of Activated Internal Alkynes: Merging Pd and Energy Transfer Catalysis
journal contribution
posted on 2020-07-31, 22:15 authored by Javier Corpas, Pablo Mauleón, Ramón Gómez Arrayás, Juan C. CarreteroA general catalytic anti-hydroarylation of electron-deficient
internal alkynes compatible with both electron-poor and electron-rich
aryl reagents is reported. This selectivity is achieved through a
sequential syn-carbopalladation of the alkyne by
an Ar–Pd species, followed by a tandem, Ir-photocatalyzed,
counter-thermodynamic E → Z isomerization. The use of ortho-substituted boronic
acids enables direct access to pharmaceutically relevant heterocyclic
cores via a cascade process. Mechanistic insight into the involvement
of Ar–Pd versus Pd–H as an active species is provided.
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Hydroarylationsequential synorthoselectivityheterocyclic coresMechanistic insightspecieshydroarylationelectron-rich aryl reagentsaccesselectron-poorMerging Pdcounter-thermodynamiccascade processActivated Internal Alkynespharmaceuticallytandeminvolvementboronic acidsIr-photocatalyzedEnergy Transfer Catalysisalkynecarbopalladationelectron-deficientArisomerization
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