anti-Hydroarylation of Activated Internal Alkynes: Merging Pd and Energy Transfer Catalysis

A 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-photocatal...

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Veröffentlicht in:	Organic letters 2020-08, Vol.22 (16), p.6473-6478
Hauptverfasser:	Corpas, Javier, Mauleón, Pablo, Gómez Arrayás, Ramón, Carretero, Juan C
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Sprache:	eng
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description	A 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.
doi_str_mv	10.1021/acs.orglett.0c02281
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title	anti-Hydroarylation of Activated Internal Alkynes: Merging Pd and Energy Transfer Catalysis
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