Abstract
Cyclic alk-2-ynyl carbonates, easily prepared from propargylic alcohols and carbon dioxide without phosgene derivatives, are useful synthetic substrates. Their activation with suitable palladium catalyst precursors leads to reactive zwitterionic allenyl palladium species and offers straightforward routes to functional a-allenols derivatives upon hydrogenolysis, coupling with terminal alkynes and monocarbonylation. The specificity of these cyclic carbonates as compared to acyclic propargylic derivatives, due to the presence of the reactive homopropargylic oxygen atom, is evidenced by the synthesis of oxygenated heterocycles resulting from double carbonylation, and dihydrofurans formed by coupling with electron deficient olefins.
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