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

A systematic study into the Sonogashira cross-coupling of 1,1'-diiodoferrocene (fcl(2)) confirms that the Pd(0)-P(Bu-t)(3) system provides a remarkable rate increase over Pd(0)-(PPh3)(2). Attempts to couple 4-ethynylphenylthioacetate (2) with fcl(2) instead produced a novel cyclic trimer of the...

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Published inChemical communications (Cambridge, England) Vol. 49; no. 50; pp. 5663 - 5665
Main Authors Inkpen, Michael S., White, Andrew J. P., Albrecht, Tim, Long, Nicholas J.
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 01.01.2013
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
ARYL BROMIDES
ACETYLENE DERIVATIVES
POLYMERS
FERROCENE
MOLECULAR WIRES
COMPLEXES
PURIFICATION
CATALYST
POLYFERROCENYLALKYNE LINKAGES
RECEPTORS
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Summary:A systematic study into the Sonogashira cross-coupling of 1,1'-diiodoferrocene (fcl(2)) confirms that the Pd(0)-P(Bu-t)(3) system provides a remarkable rate increase over Pd(0)-(PPh3)(2). Attempts to couple 4-ethynylphenylthioacetate (2) with fcl(2) instead produced a novel cyclic trimer of the former, from syn addition of S-Ac across C C.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1359-7345
1364-548X
DOI:10.1039/c3cc43116a