Journal
NATURE CHEMISTRY
Volume 1, Issue 6, Pages 482-486Publisher
NATURE RESEARCH
DOI: 10.1038/NCHEM.331
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Funding
- NIHGMS
- Bristol-Myers Squibb
- Novartis
- ARO-DURIP
- ONR-DURIP
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The last decade has witnessed dramatic growth in the number of reactions catalysed by electrophilic gold complexes. Although proposed mechanisms often invoke the intermediacy of gold-stabilized cationic species, the nature of bonding in these intermediates remains unclear. Herein, we propose that the carbon-gold bond in these intermediates comprises varying degrees of both sigma- and pi-bonding; however, the overall bond order is generally less than or equal to one. The bonding in a given gold-stabilized intermediate, and the position of this intermediate on a continuum ranging from gold-stabilized singlet carbene to gold-coordinated carbocation is dictated by the carbene substituents and the ancillary ligand. Experiments show that the correlation between bonding and reactivity is reflected in the yield of gold-catalysed cyclopropanation reactions.
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