Abstract
The ever-increasing role of homogeneous gold catalysis in organic synthesis and the consequent need to be able to rationally control the rate and outcome of such reactions has emphasised the importance of each successive metal–carbon coordination step. Concentrating on alkyne and allene cyclisation and upon reaction mechanisms postulated on the basis of empirical and theoretical results, we have examined the coordination of gold fragments to triple bonds, the modification of gold(I) precatalysts to effect specific reaction pathways or enantioselectivity and the isolation of coordinated intermediates or model compounds thereof. Some of the recent advances that have been made in various laboratories are described in this compact review.
Highlights
Zeise in 1827 that ethylene forms a complex with a low-valent platinum salt was the key discovery that led to the development of one of the most important branches of organometallic chemistry, and had an enormous economic impact through its relevance to catalysis of organic transformations
Half a century later, homogeneous gold catalysts are in focus of worldwide research. They have become the reagents of choice mainly for a large variety of processes used in the synthesis of high-value fine chemicals, and may soon even enter the production of commodities
Confining ourselves mostly to intramolecular addition reactions catalysed by gold(I) compounds, impressive developments in clarifying the consecutive changes in gold coordination during the total process have been described
Summary
Affiliations: 1Department of Chemistry and Polymer Science, University of Stellenbosch, South Africa. Gold coordination during homogeneous alkyne and allene cyclisation catalysis: Coordination to substrates, to ancillary ligands and in intermediates. The ever-increasing role of homogeneous gold catalysis in organic synthesis and the consequent need to be able to rationally control the rate and outcome of such reactions has emphasised the importance of each successive metal–carbon coordination step. Concentrating on alkyne and allene cyclisation and upon reaction mechanisms postulated on the basis of empirical and theoretical results, we have examined the coordination of gold fragments to triple bonds, the modification of gold(I) precatalysts to effect specific reaction pathways or enantioselectivity and the isolation of coordinated intermediates or model compounds thereof. Some of the recent advances that have been made in various laboratories are described in this compact review
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