Synthesis of Aziridines by Palladium-Catalyzed Reactions of Allylamines with Aryl and Alkenyl Halides: Evidence of a syn-Carboamination Pathway

摘要

Palladium-catalyzed intramolecular carboetherification or carboamination reactions of alkenes with organic halides emerged as an attractive method to construct heterocycles, forming both carbon-heteroatom and carbon-carbon bonds in a single operation. A number of five-membered heterocycles have been synthesized by this methodology, however, the preparation of strained three-membered heterocycles has remained a challenge. We have previously reported palladium-catalyzed carboetherification reactions of tertiary allyl alcohols with aryl or alkenyl halides, which provide multisubstituted epoxides. We expected that the reaction could be extended to carboamination for the synthesis of aziridines starting from allylamines. Herein we present our preliminary results of the carboamination along with evidence for a plausible reaction mechanism.