%0 Journal Article %J Journal of Organic Chemistry %D 2019 %T External oxidant-dependent reactivity switch in copper-mediated intramolecular carboamination of alkynes: access to a different class of fluorescent ionic nitrogen-doped polycyclic aromatic hydrocarbons %A Shaikh, Aslam C. %A Banerjee, Somsuvra %A Mule, Ravindra D. %A Bera, Saibal %A Patil, Nitin T. %X

An interesting case of external oxidant-controlled reactivity switch leading to a divergent set of ionic nitrogen-doped polycyclic aromatic hydrocarbons (N-doped PAHs), is presented here, which is quite unrecognized in copper-mediated reactions. In the current scenario, from the same pyridino-alkyne substrates, the use of the external oxidant Ph1(0Ac)2, in combination with Cu(OTf)(2), gave N-doped spiro-PAHs via a dearomative 1,2-carboamination process; whereas, without the use of oxidant, an alkyne/azadiene [4 + 2]-cycloaddition cascade occurred to exclusively afford ionic N-doped PAHs. These newly synthesized N-doped PAHs further exhibit tunable emissions, as well as excellent quantum efficiencies.

%B Journal of Organic Chemistry %V 84 %P 4120-4130 %8 APR %G eng %N 7 %9 Article %3

Foreign

%4

4.745

%R 10.1021/acs.joc.9b00120