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Paper | Regular issue | Vol 91, No. 3, 2015, pp.561-572
Published online, 3rd February, 2015
DOI: 10.3987/COM-14-13162
Decarboxylative Halogenation of Indolecarboxylic Acids Using Hypervalent Iodine(III) Reagent and Its Application to the Synthesis of Polybromoindoles

Hiromi Hamamoto,* Hideaki Umemoto, Misako Umemoto, Chiaki Ohta, Emi Fujita, Akira Nakamura, Tomohiro Maegawa, and Yasuyoshi Miki*

*Department of Applied Biological Chemistry, Faculty of Agriculture, Meijo University, 1-501 Shiogamaguchi, Tempaku-ku, Nagoya, Japan

Abstract

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.