Gold Catalysis

Gold catalyzed cycle for a wide-ranging alkyne and alkene activation for addition of nucleophileAu-cycle

Homogeneous gold catalysis

We have developed a method to create instant cationic, catalytically active, gold nuclei induced by pyridine tethered in NHC ligand carrying gold specie (AuCl3).


We have extablished a direct Au(III) catalysed route from enynamines to cyclopentadienes (Cp). Initially, we thought that isolated zwitterionic Au(III)cyclopentadiene would play a key role in the mechanistic pathway (CEJ 2010).

Cp-JOC Abs


Recently, we have discovered that the chirality is transferred from the amine moiety to the bridgehead of Cp (JOC 2014). Theoretical and experimental studies suggest in concert that a unique dual gold push-pull transition state is involved in the alkene cis-trans isomerization step, while chirality is transferred via a helical shape transtion state with allenic character.

Cp Mechanistic cycle




Related publications

T. Wirtanen, M. Muuronen, M. Melchionna, M. Patzschke, J. Helaja: Gold(III)-Catalyzed Enynamine–Cyclopentadiene Cycloisomerization with Chirality Transfer: An Experimental and Theoretical Study Indicating Involvement of Dual Au(III) Push–Pull Assisted cistrans Isomerism J. Org. Chem. 2014, 79, 10269–10283.

J .E. Perea-Buceta, T. Wirtanen, O.-V. Laukkanen, M. K. Mäkelä, M. Nieger, M. Melchionna, N. Huittinen, J. A. Lopez-Sanchez, J. Helaja: Cycloisomerization of 2-Alkynylanilines to Indoles Catalyzed by Carbon-Supported Gold Nanoparticles and Subsequent Homocoupling to 3,3’-Biindoles Angew. Chem. Int. Ed. 2013, 52, 11835-11839.

M. Muuronen, J. Perea-Buceta, M. Nieger, M. Patzschke, J. Helaja: Cationic Gold Catalysis with Pyridine-Tethered Au(III) NHC-Carbenes: An Experimental and DFT Computational Study Organometallics 2012, 31, 4320-4330.

M. Melchionna, M. Nieger, J. Helaja: Isolation of a Zwitterionic Dienegold(III) Complex Intermediate in Direct Enyne-amine to Cyclopentadiene Conversion Chemistry A European Journal 2010, 16, 8262-8267.