Three-Component Reaction for the Synthesis of Highly Functionalized Propargyl Ethers
Multicomponent reactions provide efficient means to access molecular complexity. Herein, we report a copper-catalyzed three-component reaction of diazo compounds, alcohols and ethynyl benziodoxole (EBX) reagents for the synthesis of propargyl ethers. Extensive variations of the three partners of the reaction is possible, leading to highly functionalized and structurally diverse products under mild conditions. Alkynylation of a copper ylide intermediate is postulated as key step for this transformation.
Propargylic oxidations catalyzed by dirhodium caprolactamate in water: Efficient access to α,β-acetylenic ketones
(Chemical Equation Presented) Dirhodium(II) caprolactamate (1, Rh 2(cap)4) with 70% w/w aqueous tert-butyl hydroperoxide (T-HYDRO) is a highly effective catalytic oxidation protocol for the selective C-H oxidation of alkynes to propargylic ketones. The oxidation occurs readily in aqueous solvent under mild conditions with an inexpensive and easily handled oxidant. α,β-Acetylenic carbonyl compounds are formed in up to 80% isolated yield.
McLaughlin, Emily C.,Doyle, Michael P.
p. 4317 - 4319
(2008/09/20)
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