This account describes our recent work on catalytic cross-coupling reactions using carboxylate and carbonate leaving groups in the electrophilic substrate. Some bisphosphine-chelated palladium(O) complexes are effective for the cleavage of benzylic C-O bonds in benzyl carbonates and acetates. This C-O bond cleavage was utilized in catalytic reactions of these benzylic esters; the nucleophilic benzylic substitutions and the crosscoupling reactions with organometallic compounds. Furthermore, vinyl acetate was proved to work as the coupling partner of arylboronates in the presence of [RhCl(cod)] 2-DPPB. Interestingly, the organoborons react selectively at the position β to the leaving group in the alkenyl ester when the rhodium-catalyzed reaction is conducted in the absence of the bisphosphine.
|Number of pages||8|
|Journal||Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry|
|Publication status||Published - Nov 2011|
All Science Journal Classification (ASJC) codes
- Organic Chemistry