Issue 19, 2015

Alkynylation of steroids via Pd-free Sonogashira coupling

Abstract

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.

Graphical abstract: Alkynylation of steroids via Pd-free Sonogashira coupling

Supplementary files

Article information

Article type
Paper
Submitted
19 Mar 2015
Accepted
08 Apr 2015
First published
08 Apr 2015

Org. Biomol. Chem., 2015,13, 5542-5555

Author version available

Alkynylation of steroids via Pd-free Sonogashira coupling

Y. N. Kotovshchikov, G. V. Latyshev, N. V. Lukashev and I. P. Beletskaya, Org. Biomol. Chem., 2015, 13, 5542 DOI: 10.1039/C5OB00559K

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