6‑Aroylated Phenanthridines via Base Promoted Homolytic Aromatic Substitution (BHAS)

6‑Aroylated Phenanthridines via Base Promoted Homolytic Aromatic Substitution (BHAS)

Readily accessible 2-isocyanobiphenyls react with aromatic aldehydes via base promoted homolytic aromatic substitution (BHAS) to give 6-aroylated phenanthridines. Reactions occur via addition of acyl radicals to the isonitrile functionality and subsequent intramolecular BHAS of the intermediate imid...

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Veröffentlicht in:Organic letters 2013-12, Vol.15 (24), p.6286-6289
Hauptverfasser: Leifert, Dirk, Daniliuc, Constantin Gabriel, Studer, Armido
Format: Artikel
Sprache:eng
Schlagworte:
Aldehydes - chemistry
Crystallography, X-Ray
Models, Molecular
Molecular Structure
Phenanthridines - chemical synthesis
Phenanthridines - chemistry
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Zusammenfassung:Readily accessible 2-isocyanobiphenyls react with aromatic aldehydes via base promoted homolytic aromatic substitution (BHAS) to give 6-aroylated phenanthridines. Reactions occur via addition of acyl radicals to the isonitrile functionality and subsequent intramolecular BHAS of the intermediate imidoyl radicals. Initiation of the radical chain reaction is best achieved with small amounts of FeCl3 (0.4 mol %), and the commercially available and cheap tBuOOH is used as the oxidant.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol403147v