Arynes in the Synthesis of N-Arylisatins

Significance

Reported is an efficient synthesis of isatins from the reaction of in situ generated arynes with methyl 2-oxo-2-(arylamino)acetates by simply stirring the reagents overnight in MeCN with a large excess of CsF. The yields range from mediocre to good, and the scope was well studied. The yields are slightly lower with electron-poor aryne substrates compared to electron-rich substrates. The reaction fails utterly for nitro-substituted substrates, which is attributed to a reaction of the aryne with the nitro group, behavior ­observed by the authors also previously (D. C. Rogness, R. C. Larock Tetrahedron Lett. 2009, 50, 4003).