Silylium-Catalyzed Alkynylation and Etherification Reactions of Benzylic Acetates

Addition of catalytic amounts of bistriflimide triggers useful coupling reactions of benzyl acetates with trimeth-ykalkynyl)silanes and trimethyl(alkoxy)silanes to afford propargyl arenes and benzyl alkyl ethers, respectively. The added acid assists the release of reactive trimethylsilylium ion into the reaction media, which were found to act as the ultimate catalytic species responsible for the C-C and the C-O forming steps. The cationic nature of these coupling processes is documented.

Automated summary

The addition of catalytic amounts of bistriflimide triggers useful coupling reactions between benzyl acetates and trimethyl(alkynyl)silanes as well as trimethyl(alkoxy)silanes, resulting in the formation of propargyl arenes and benzyl alkyl ethers, respectively. The added acid facilitates the release of reactive trimethylsilylium ion into the reaction media, which acts as the ultimate catalytic species responsible for the formation of C-C and C-O bonds. The cationic nature of these coupling processes is confirmed.