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N-Methyl Transfer Induced Copper-Mediated Oxidative Diamination of Alkynes

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JournalOrganic Letters
DatePublished - 6 May 2016
Issue number10
Volume18
Number of pages4
Pages (from-to)2487-2490
Original languageEnglish

Abstract

A novel intramolecular oxidative diamination of bis(2-aminophenyl)acetylene for the synthesis of the structurally intriguing π-conjugated polyheterocyclic scaffold, 5,10-dihydroindolo[3,2-b]indole (DHII), has been developed under Cu(hfacac)2/O2 oxidation systems. The structure design of bis(2-aminophenyl)acetylene bearing both N,N-dimethylamine and primary amine groups is crucial for constructing the corresponding DHII scaffold. Notably, an intermolecular N-methyl transfer from the nitrogen atom of N,N-dimethylamine to the primary amine takes place, which is a critical step for the successful implementation of the present annulation process.

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