Nickel-Catalyzed Hydroarylation of in Situ Generated 1,3-Dienes with Arylboronic Acids Using a Secondary Homoallyl Carbonate as a Surrogate for the 1,3-Diene and Hydride Source

The nickel-catalyzed hydroarylation of 1,3-dienes with arylboronic acids using a secondary homoallyl carbonate as a surrogate for the 1,3-diene and hydride source has been developed. The synthetic strategy allowed an efficient access to a wide array of hydroarylation products in high yields with hig...

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Veröffentlicht in:Organic letters 2020-02, Vol.22 (3), p.1124-1129
Hauptverfasser: Hamaguchi, Takashi, Takahashi, Yoshiyuki, Tsuji, Hiroaki, Kawatsura, Motoi
Format: Artikel
Sprache:eng
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Zusammenfassung:The nickel-catalyzed hydroarylation of 1,3-dienes with arylboronic acids using a secondary homoallyl carbonate as a surrogate for the 1,3-diene and hydride source has been developed. The synthetic strategy allowed an efficient access to a wide array of hydroarylation products in high yields with high functional group compatibility without the use of an external hydride source. Mechanistic experiments indicated that the alkene-directed oxidative addition and subsequent β-hydride elimination would be a critical process in this transformation.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b04634