Synlett

Hypervalent Iodine (III) Mediated Decarboxylative Halogenation of Indolecarboxylic Acids for the Synthesis of Haloindole Derivatives

…, H Umemoto, M Umemoto, C Ohta, M Dohshita, Y Miki

Index: Hamamoto, Hiromi; Umemoto, Hideaki; Umemoto, Misako; Ohta, Chiaki; Dohshita, Masashi; Miki, Yasuyoshi Synlett, 2010 , # 17 p. 2593 - 2596

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Citation Number: 6

Abstract

Abstract The treatment of 1-methylindole-2, 3-dicarboxylic acid with hypervalent iodine (III) reagent, phenyliodine diacetate (PIDA), in the presence of lithium bromide gave 1-methyl-3, 3-dibromooxindole. However, the reaction of 1-(phenylsulfonyl) indole-2, 3-dicarboxylic acid with PIDA in the presence of lithium bromide afforded 2, 3-dibromo-1-(phenylsulfonyl) indole. In a similar manner, the 2, 3-dichloro-and 2, 3-diiodo-indole derivatives were ...

~86%

~87%

~74%

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