A cationic gold(I)-catalyzed decarboxylative etherification of propargyl carbonates to selectively produce propargyl ethers is reported. In the reaction the gold(I) catalyst shows a distinct sigma-Lewis acidity rather than the commonly observed pi-Lewis acidity, and thus catalyzes the decarboxylation of a variety of propargyl carbonates to give the corresponding propargyl ethers with high selectivity. This reaction represents a rare example of the tunable reactivity of cationic gold(I) complexes between sigma-Lewis acidity and pi-Lewis acidity.

decarboxylation; gold catalysis; pi-Lewis acids; sigma-Lewis acids; propargyl carbonates

Nanchang University