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Regio- and chemoselective hydroamination of unactivated alkenes with anthranils via NiH-catalysis.

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A NiH-catalyzed polarity-reversed hydroamination of β,γ-, γ,δ- and δ,ε-unsaturated alkenes with electrophilic anthranils was developed. This reaction proceeds in a highly regio- and chemoselective manner to afford γ, δ and… Click to show full abstract

A NiH-catalyzed polarity-reversed hydroamination of β,γ-, γ,δ- and δ,ε-unsaturated alkenes with electrophilic anthranils was developed. This reaction proceeds in a highly regio- and chemoselective manner to afford γ, δ and ε-arylamines bearing a carbonyl or alcohol functionality with 100% atom efficiency. Preliminary mechanistic studies indicate that the chemoselectivity is controlled by the base and the alcohol product is derived from the base-catalyzed hydrosilylation of the CO bond.

Keywords: hydroamination unactivated; regio chemoselective; hydroamination; chemoselective hydroamination; alkenes anthranils; unactivated alkenes

Journal Title: Chemical communications
Year Published: 2023

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