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An unexpected fluorination‐oxidation of 2‐hydroxymethylindole using selectfluor under mild condi‐tions without a catalyst is described. This new chemistry allows for efficient and rapid synthesis of various 3‐fluoroindole‐2‐aldehydes and novel quaternary 3‐fluoro‐3‐hydroxymethyl‐2‐oxindoles with up to 86% isolated yield.
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