Alkynylation of steroids via Pd-free Sonogashira coupling

Alkynylation of steroids via Pd-free Sonogashira coupling

Cu-catalyzed Pd-free Sonogashira coupling has been proposed as a straightforward and convenient route to valuable steroidal enynes. A biligand catalyst system based on Ph3P and TMEDA has been designed. The protocol was utilized for the efficient coupling of iodosteroids with diverse terminal alkynes...

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Veröffentlicht in:Organic & biomolecular chemistry 2015-05, Vol.13 (19), p.5542-5555
Hauptverfasser: Kotovshchikov, Yury N, Latyshev, Gennadij V, Lukashev, Nikolay V, Beletskaya, Irina P
Format: Artikel
Sprache:eng
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Zusammenfassung:Cu-catalyzed Pd-free Sonogashira coupling has been proposed as a straightforward and convenient route to valuable steroidal enynes. A biligand catalyst system based on Ph3P and TMEDA has been designed. The protocol was utilized for the efficient coupling of iodosteroids with diverse terminal alkynes and 1-trimethylsilylalkynes. A possible role of an auxiliary ligand as a phase-transfer catalyst for a sparingly soluble inorganic base (K2CO3) was revealed.
ISSN:1477-0520
1477-0539
DOI:10.1039/c5ob00559k