Synthesis of 2,3-disubstituted indoles from alkynylanilines and 2-chlorophenols using palladium–dihydroxyterphenylphosphine catalyst

[Display omitted] •Synthesis of 2,3-disubstituted indoles bearing 2-hydroxyphenyl groups at the C3 positions has been achieved.•Readily available chlorophenols can be used as substrates.•Only the Pd–DHTP catalyst can effectively catalyze the desired reaction.•2-Chloro group of 2,4-dichlorophenol rea...

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Veröffentlicht in:Tetrahedron letters 2020-05, Vol.61 (21), p.151896, Article 151896
Hauptverfasser: Yamaguchi, Miyuki, Ogihara, Kota, Konishi, Hideyuki, Manabe, Kei
Format: Artikel
Sprache:eng
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Zusammenfassung:[Display omitted] •Synthesis of 2,3-disubstituted indoles bearing 2-hydroxyphenyl groups at the C3 positions has been achieved.•Readily available chlorophenols can be used as substrates.•Only the Pd–DHTP catalyst can effectively catalyze the desired reaction.•2-Chloro group of 2,4-dichlorophenol reacts selectively. 2,3-Disubstituted indoles bearing 2-hydroxyphenyl moieties at their C3 positions were synthesized from readily available 2-chlorophenols and alkynylanilines via aminopalladation/reductive elimination using Pd–dihydroxyterphenylphosphine catalyst. The catalyst accelerates the introduction of the 2-hydroxyphenyl group at the C3 position of the indole.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2020.151896