Reversed-Polarity Synthesis of N-Sulfonyl Ketimines with Imidoylsilanes and Diaryliodonium Salts via Palladium-Catalyzed Reactions.

Abstract

Imines are important building blocks in organic chemistry. Iminines, aldimines and ketimines, have been traditionally synthesized by the condensation reaction of the corresponding carbonyl compound with an amine moiety. More recently, palladium-catalyzed synthesis of ketimines using imidoyl chlorides has been reported. As an alternative, we report the reversed-polarity synthesis of N-sulfonyl ketimines using an anion equivalent imidoylsilane as a new nucleophilic coupling partner in the presence of a palladium catalyst. To the best of our knowledge, this is the first report of the use of imidoylsilanes in transition-metal-catalyzed coupling reactions. Diaryliodonium salt as an electrophile, various aryl-aryl or heteroaryl-aryl N-sulfonyl ketimines were successfully prepared in up to 99% isolated yields.