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
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