Highly selective palladium–benzothiazole carbene-catalyzed allylation of active methylene compounds under neutral conditions

Abstract

The Pd–benzothiazol-2-ylidene complex I was found to be a chemoselective catalyst for the Tsuji–Trost allylation of active methylene compounds carried out under neutral conditions and using carbonates as allylating agents. The proposed protocol consists in a simplified procedure adopting an in situ prepared catalyst from Pd2dba3 and 3-methylbenzothiazolium salt V as precursors. A comparison of the performance of benzothiazole carbene with phosphanes and an analogous imidazolium carbene ligand is also proposed.

Keywords

• active methylene compounds
• allylic carbonates
• Pd–benzothiazol-2-ylidene complex
• Tsuji–Trost allylation