6‑Phosphorylated Phenanthridines from 2‑Isocyanobiphenyls via Radical C–P and C–C Bond Formation

A C–P bond and a C–C bond are formed in the synthesis of 6-phosphorylated phenanthridines starting with readily prepared 2-isocyanobiphenyls and commercially available P-radical precursors. The radical cascade reaction comprises addition of an oxidatively generated P-centered radical to the isonitri...

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Veröffentlicht in:Organic letters 2014-01, Vol.16 (1), p.250-253
Hauptverfasser: Zhang, Bo, Daniliuc, Constantin Gabriel, Studer, Armido
Format: Artikel
Sprache:eng
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Zusammenfassung:A C–P bond and a C–C bond are formed in the synthesis of 6-phosphorylated phenanthridines starting with readily prepared 2-isocyanobiphenyls and commercially available P-radical precursors. The radical cascade reaction comprises addition of an oxidatively generated P-centered radical to the isonitrile functionality and subsequent homolytic aromatic substitution. Various 6-phosphorylated phenanthridines are formed in moderate to excellent yield. In contrast to the currently intensively investigated direct arene phosphorylation, the arene core is constructed with concomitant phosphorylation using this approach.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol403256e