TY - JOUR T1 - 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 JF - Journal of Organic Chemistry Y1 - 2019 A1 - Shaikh, Aslam C. A1 - Banerjee, Somsuvra A1 - Mule, Ravindra D. A1 - Bera, Saibal A1 - Patil, Nitin T. AB -

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.

VL - 84 IS - 7 U3 -

Foreign

U4 -

4.745

ER -