Palladium-Catalyzed Chemoselective Aminomethylative Cyclization and Aromatizing Allylic Amination: Access to
Bangkui Yu1, Houjian Yu1, Hanmin Huang1,2
1Hefei National Laboratory for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China, Hefei 230026, P. R. China.
Abstract:
A palladium-catalyzed chemoselective aminomethylative cyclization and aromatizing allylic amination of enyne-tethered allylic alcohols with aminals is described. Under the reaction conditions, the cationic vinyl allylpalladium species undergoes selective migratory insertion of alkenes rather than reductive elimination with nucleophiles. This strategy provides an efficient and unique approach to the construction of functionalized naphthalenes, which are important building blocks in synthetic organic chemistry. Mechanistic studies have revealed that the selective sequential migratory insertion of enyne and alkene is crucial for the cyclization.
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