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

Michael S. Inkpen | Zendy; Andrew J. P. White | Zendy; Tim Albrecht | Zendy; Nicholas J. Long | Zendy

Open Access

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

Author(s) -

Michael S. Inkpen,

Andrew J. P. White,

Tim Albrecht,

Nicholas J. Long

Publication year - 2013

Publication title -

chemical communications

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.837

H-Index - 333

eISSN - 1364-548X

pISSN - 1359-7345

DOI - 10.1039/c3cc43116a

Subject(s) - sonogashira coupling , coupling (piping) , chemistry , combinatorial chemistry , stereochemistry , materials science , organic chemistry , palladium , metallurgy , catalysis

A systematic study into the Sonogashira cross-coupling of 1,1'-diiodoferrocene (fcI2) confirms that the Pd(0)-P((t)Bu)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≡C.

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