Regioselective and Stereoselective Entry to β,β-Disubstituted Vinyl Ethers via the Sequential Hydroboration/Suzuki-Miyaura Coupling of Ynol Ethers

A highly regio- and stereoselective synthesis of stereodefined beta,beta-disubstituted alkenyl ethers featuring the sequential hydroboration/Suzuki-Miyaura coupling of ynol ethers has been described. A number of functional groups, including OMe, Ac, CO2Et, CN, halides, and alkyl, (hetero)aryl, and alkenyl groups, are well-tolerated under the reaction conditions. Furthermore, it allows a facile entry to the labile diarylacetaldehydes by TFA-mediated hydrolysis of beta,beta-disubstituted vinyl ethers.