Issue 50, 2013
From the journal:

Chemical Communications

Rapid Sonogashira cross-coupling of iodoferrocenes and the unexpected cyclo-oligomerization of 4-ethynylphenylthioacetate†

Michael S. Inkpen,a   Andrew J. P. White,a   Tim Albrecht*a  and  Nicholas J. Long*a  

* Corresponding authors

a Department of Chemistry, Imperial College London, London, UK
E-mail: n.long@imperial.ac.uk, t.albrecht@imperial.ac.uk
Tel: +44 (0)20 7594 5781

Abstract

A systematic study into the Sonogashira cross-coupling of 1,1′-diiodoferrocene (fcI2) confirms that the Pd(0)–P(tBu)3 system provides a remarkable rate increase over Pd(0)–(PPh3)2. Attempts to couple 4-ethynylphenylthioacetate (2) with fcI2 instead produced a novel cyclic trimer of the former, from syn addition of S–Ac across C[triple bond, length as m-dash]C.

Graphical abstract: Rapid Sonogashira cross-coupling of iodoferrocenes and the unexpected cyclo-oligomerization of 4-ethynylphenylthioacetate

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Article information

DOI
https://doi.org/10.1039/C3CC43116A
Article type
Communication
Submitted
26 Apr 2013
Accepted
13 May 2013
First published
14 May 2013

Chem. Commun., 2013,49, 5663-5665

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Rapid Sonogashira cross-coupling of iodoferrocenes and the unexpected cyclo-oligomerization of 4-ethynylphenylthioacetate

M. S. Inkpen, A. J. P. White, T. Albrecht and N. J. Long, Chem. Commun., 2013, 49, 5663 DOI: 10.1039/C3CC43116A

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