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Gold-catalyzed oxidation of alkynes
Although both alkynes and alkenes form stable complexes with gold,[1] alkynes are selectively activated by gold(I) in the presence of alkenes or other functional groups.[2] This high alkynophilicity of gold(I) actually reflects the higher reactivity of-alkyne gold(I) complexes over-alkene gold(I) complexes toward attack by a wide range of nucleophiles,[ 3] which is the basis for the surge in activity for synthetic applications based on the selective activation of alkynes in complex molecular settings.[2,4-6] The gold-catalyzed oxidation of alkynes takes place with oxidants with a highly polar X+-O-bond, such as sulfoxides and amine N-oxides,[7,8] which attack thealkyne gold(I) complex in a process similar to the addition of alcohols and water to alkynes, one of the prototypical transformations catalyzed by gold.[9-11] This addition reaction gives preferentially or exclusively products of Markovnikov addition[12,13] and can be performed with low catalyst loadings.[14] Two reviews have been published very recently covering developments in the gold(I)-catalyzed oxidation of alkynes.[7,8].
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Reference£º
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem