Catalytic alkene difunctionalization presents an attractive and powerful strategy for introducing molecular complexity and structural diversity with has wide applications in organic synthesis. Yet a compelling challenge that remains to be solved is that the aminoheteroarylation of unactivated alkenes for installing electron-rich amines and diverse heteroarenes in a selective and modular manner. Our lab has developed a copper-catalyzed aminoheteroarylation of unactivated alkenes for the synthesis of 1,2 amino heteroaryl motifs. The transformation is initiated by a copper-catalyzed electrophilic amination of the alkene followed by an alcohol-assisted heteroaryl migration. This method features a broad scope of diverse amines, heteroaryl groups, and alkenes, as well as good tolerance of functional groups under mild conditions. This amino heteroarylation strategy has been extendable on the α-tertiary amide-assisted heteroaryl migration as well as on the rapid formation of medium-size rings via ring expansion.

Copper-catalyzed aminoheteroarylation of unactivated alkenes through distal heteroaryl migration

ACS Fall 2021

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