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A palladium-catalyzed, three-component reaction between propargylic alcohols, CO2, and aryl halides was developed whereby a sequential carboxylation, trans-oxopalladation of the C≡C bond by an ArPdX species, and a reductive elimination… Click to show full abstract
A palladium-catalyzed, three-component reaction between propargylic alcohols, CO2, and aryl halides was developed whereby a sequential carboxylation, trans-oxopalladation of the C≡C bond by an ArPdX species, and a reductive elimination procedure afforded a series of functionalized α-alkylidene cyclic carbonates in moderate to excellent yields. Notably, the configuration of these tetrasubstituted olefins was dominated by the trans-oxopalladation step where the aryl group derived from ArX is located trans to the oxygen attached in the double bond. This protocol features simultaneous formation of four novel bonds in a one-pot reaction, representing an efficient method for incorporation of CO2 into heterocycles.
Journal Title: Organic letters
Year Published: 2017
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