Oxidative dearomatization of indoles with 70 % aqueous tert‐butylhydroperoxide (TBHP) in the absence of any metal salts/organic solvents gave the corresponding C2/C3‐quaternary indolinones under open‐air reaction conditions. The nature of substituent on the indole nitrogen dictates the type of product formed in these reactions. Free (NH)‐indoles gave C2‐quaternary indolinone derivatives whilst (NR)‐indoles yielded C3‐quaternary indolinones as the major product. Moreover, the addition of an excess amount of TBHP also facilitated the one‐pot transformation of (NR)‐indoles to the corresponding isatin derivatives.

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6-Exo-trig cyclization reaction through regioselective carbopalladation was demonstrated with N-(2-halobenzyl)-N-allylamines to furnish the corresponding C4-substituted tetrahydroisoquinoline derivatives.

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