DECARBOXYLATIVE HALOGENATION OF INDOLECARBOXYLIC ACIDS USING HYPERVALENT IODINE(III) REAGENT AND ITS APPLICATION TO THE SYNTHESIS OF POLYBROMOINDOLES

作者：Hamamoto Hiromi^*; Umemoto Hideaki; Umemoto Misako; Ohta Chiaki; Fujita Emi; Nakamura Akira; Maegawa Tomohiro; Miki Yasuyoshi

来源：Heterocycles, 2015, 91(3): 561-572.

DOI：10.3987/COM-14-13162

• Indole
• Hypervalent Iodine
• Marine Natural Product
• Halogenation Reaction
• Decarboxylation Reaction

Hypervalent iodine mediated decarboxylative halogenation of indoledicarboxylic acid derivatives was studied. The treatment of 1-methylindole-2,3-dicarboxylic acid with phenyliodine diacetate (PIDA) in the presence of lithium bromide gave 1-methyl-3,3-bromooxindole. 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-diiodoindole derivatives could be obtained by the reaction of the indole-2,3-dicarboxylic acids with PIDA in the presence of lithium chloride and iodide. This method was optimized to the synthesis of polybromoindole alkaloids.

• 出版日期2015-3-1