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Synlett 2011(11): 1563-1566  
DOI: 10.1055/s-0030-1260791
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Hypervalent Iodine(III)-LiX Combination in Fluoroalcohol Solvent for Aromatic Halogenation of Electron-Rich Arenecarboxylic Acids

Hiromi Hamamoto, Sho Hattori, Kaori Takemaru, Yasuyoshi Miki*
School of Pharmaceutical Sciences, Kinki University, 3-4-1 Kowakae, Higashi-Osaka 577-8502, Japan
Fax: +81(6)67212505; e-Mail: y_miki@phar.kindai.ac.jp;
Further Information

Publication History

Received 12 March 2011
Publication Date:
15 June 2011 (online)

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Abstract

The novel reagent system, PhI(OAc)2-LiX combination in fluoroalcohol solvents, was found to be effective for halodecarboxylation of electron-rich arenecarboxylic acids. The method provided an efficient route to halogenated phenol ether derivatives.

Key words

carboxylic acids - hypervalent iodine - halogenation - fluoroalchol - decarboxylation

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14

Compound 3b was also obtained as minor product into the iodination of 1a where 3b was not converted to 4b smoothly (<10%) in further iodination reaction [PhI(OAc)2/LiI combination in HFIP].