Copper-Catalyzed Oxidative Ring Closure and Carboarylation of 2‑Ethynylanilides

Copper-Catalyzed Oxidative Ring Closure and Carboarylation of 2‑Ethynylanilides

A new copper-catalyzed oxidative ring closure of ethynyl anilides with diaryliodonium salts was developed for the highly modular construction of benzoxazines bearing a fully substituted exo double bond. The oxidative transformation includes an unusual 6-exo-dig cyclization step with the formation of...

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Veröffentlicht in:Organic letters 2013-11, Vol.15 (22), p.5654-5657
Hauptverfasser: Sinai, Ádám, Mészáros, Ádám, Gáti, Tamás, Kudar, Veronika, Palló, Anna, Novák, Zoltán
Format: Artikel
Sprache:eng
Schlagworte:
Anilides - chemistry
Benzoxazines - chemical synthesis
Benzoxazines - chemistry
Catalysis
Copper - chemistry
Cyclization
Molecular Structure
Onium Compounds - chemistry
Oxidation-Reduction
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Zusammenfassung:A new copper-catalyzed oxidative ring closure of ethynyl anilides with diaryliodonium salts was developed for the highly modular construction of benzoxazines bearing a fully substituted exo double bond. The oxidative transformation includes an unusual 6-exo-dig cyclization step with the formation of C–O and C–C bonds.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol402600r