β-Ketophosphonates are an important class of carbonyl compounds which exhibit a wide range of biological activities and outstanding metal-complexing abilities. They are building blocks in organic synthesis, especially as intermediates for the synthesis of α,β-unsaturated carbonyl compounds, chrial β-hydroxy and β-hydroxy phosphonic acids. In this paper, a simple, convenient and environmentally benign method to synthesize the β-ketophosphonates from alkynylphosphonates was developed, which can be easily prepared in one step from commercial terminal alkynes. In the presence of 2.5 mol% XPhosAuSbF 6 and 3 equiv. of water in dichloroethane at room temperature, a broad range of alkynylphosphonates were converted into the corresponding β-ketophosphonates in nearly equivalent conversion through gold-catalyzed hydration reaction. The presented methodology will provide new strategies for β-ketophosphonates-type natural product and drug synthesis, which has important academic significance and application value.
β-Ketophosphonates are an important class of carbonyl compounds which exhibit a wide range of biological activities and outstanding metal-complexing abilities. They are building blocks in organic synthesis, especially as intermediates for the synthesis of α,β-unsaturated carbonyl compounds, chiral β-hydroxy and β-hydroxy phosphonic acids. In this paper, a cheap, simple, convenient and environmentally benign method to synthesize the β-ketophosphonates from alkynylphosphonates was developed, which can be easily prepared in one step from commercial terminal alkynes. In the presence of 10 mol% AgOAc and 4 equiv. of water in methanol at 110 ℃, a broad range of alkynylphosphonates were converted into the corresponding β-ketophosphonates in nearly equivalent conversion through silver/methanol-catalyzed hydration reaction. The presented methodology will provide new strategies for β-ketophosphonates-type natural product and drug synthesis, which has important academic significance and application value.
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