Applications in Organic Synthesis
AuCl3 has attracted the interest of organic chemists as a mild acid catalyst for a variety reactions, although no transformations have been commercialized. Gold(III) salts, especially Na (prepared from AuCl3 + NaCl), provide an alternative to mercury(II) salts as catalysts for reactions involving alkynes. An illustrative reaction is the hydration of terminal alkynes to produce methylketones:
Some alkynes undergo amination in the presence of gold(III) catalysts. Gold catalyses the alkylation of certain aromatic rings and a conversion of furans to phenols. For example, in acetonitrile solution, gold(III) chloride catalyses the alkylation of 2-methylfuran (sylvan) by methyl vinyl ketone at the 5-position:
The efficiency of this organogold reaction is noteworthy because both the furan and the ketone are sensitive to side-reactions such as polymerisation under acidic conditions. In some cases where alkynes are present, phenols sometimes form:
This reaction involves a rearrangement that gives a new aromatic ring.
Read more about this topic: Gold(III) Chloride
Famous quotes containing the words organic and/or synthesis:
“And what if all of animated nature
Be but organic Harps diversely framed,
That tremble into thought, as o’er them sweeps
Plastic and vast, one intellectual breeze,
At once the Soul of each, and God of all?”
—Samuel Taylor Coleridge (1772–1834)
“The spider-mind acquires a faculty of memory, and, with it, a singular skill of analysis and synthesis, taking apart and putting together in different relations the meshes of its trap. Man had in the beginning no power of analysis or synthesis approaching that of the spider, or even of the honey-bee; but he had acute sensibility to the higher forces.”
—Henry Brooks Adams (1838–1918)