01711nas a2200169 4500008004100000245012800041210006900169260000800238300001600246490000700262520105300269100002901322700001401351700002401365700002201389856013001411 2016 eng d00aSubstrate-controlled selectivity switch in the three-component coupling involving arynes, aromatic tertiary amines, and CO20 aSubstratecontrolled selectivity switch in the threecomponent cou cOCT a5424–54270 v183 a

The transition-metal-free multicomponent coupling involving arynes, aromatic tertiary amines, and CO2 is reported. The reaction exhibits switchable selectivity depending on the electronic nature of the aromatic amines used. With amines bearing electron-releasing/neutral groups as the nucleophilic trigger, the reaction afforded 2-arylamino benzoates via a nitrogen to oxygen alkyl group migration. Employing electron-deficient amines in the reaction furnished 2-aminoaryl benzoates proceeding via the aryl to aryl amino group migration resembling a Smiles rearrangement.

1 aBhojgude, Sachin, Suresh1 aRoy, Tony1 aGonnade, Rajesh, G.1 aBiju, Akkattu, T. uhttps://library.ncl.res.in/content/substrate-controlled-selectivity-switch-three-component-coupling-involving-arynes-aromatic