Mild cross-coupling of tertiary alkoxides with aryl chlorides enabled by a shelf-stable methylnaphthyl palladium NHC complex

Abstract

The catalytic coupling of tertiary alkoxides with aryl halides has a high energetic barrier, which makes KOtBu an advantageous base in cross-couplings. A palladium methylnaphthyl (MeNAP) catalyst bearing the IPentCl ligand was found to promote this C-O coupling with high efficiency, enabling the synthesis of aryl t-alkyl ethers from abundant aryl chlorides.