Allylic Ethers as Educts for Suzuki-Miyaura Couplings in Water at Room Temperature

摘要

The Pd-catalyzed Suzuki-Miyaura coupling reaction, which employs air- and moisture-stable organoboronic acids, is among the most valued of methods for C-C bond formation in organic synthesis. A broad range of electrophiles undergo cross-couplings with organoboronic acids, including alkyl, aryl, alkenyl, and alkynyl groups. However, reports on allylic partners, such as acetates, carbonates, halides and pseudohalides, are rare. Generally, a monodentate phosphine is required to obtain a π-allylpalladium intermediate, which subsequently undergoes smooth transmetalation with arylboronic acids.