Copper‐Catalysed Synthesis of Propargyl Alcohol and Derivatives from Acetylene and other Terminal Alkynes
Nikolai A. Sitte, Francesca Ghiringhelli, Grigory A. Shevchenko, Frank Röminger, A. Stephen K. Hashmi, Thomas Schaub
Abstract
Abstract A copper(I)/phosphine system that homogeneously catalyses the alkynylation of formaldehyde with acetylene or terminal alkynes is reported. Using acetylene at atmospheric pressure, the catalyst consisting of <1 mol% copper(I) phenylacetylide and a trialkyl bisphosphine ligand shows a high selectivity towards the formation of propargyl alcohol rather than 1,4‐butynediol, which is not reported for common heterogeneous copper acetylide catalysts. The biphasic water/toluene reaction mixture allows the separation of targeted products with the aqueous layer and catalyst recycling via the organic layer. magnified image
Topics & Concepts
ChemistryPropargyl alcoholAcetylenePropargylAcetylideCopperCatalysisPhosphineTolueneFormaldehydeAlcoholAqueous solutionOrganic chemistryAdsorptionPhotochemistryPolymer chemistryCatalytic Alkyne ReactionsSynthetic Organic Chemistry MethodsOxidative Organic Chemistry Reactions