Synthesis 2013; 45(22): 3125-3130
DOI: 10.1055/s-0033-1339672
paper
© Georg Thieme Verlag Stuttgart · New York

Facile Synthesis of 2-Fluoro-1,3-dicarbonyl Compounds with Aqueous Hydrofluoric Acid Mediated by Iodosylarenes

Tsugio Kitamura*
a   Department of Chemistry and Applied Chemistry, Graduate School of Science and Engineering, Saga University, Honjo-machi, Saga 840-8502, Japan   Fax: +81(952)288548   Email: kitamura@cc.saga-u.ac.jp
,
Satoshi Kuriki
a   Department of Chemistry and Applied Chemistry, Graduate School of Science and Engineering, Saga University, Honjo-machi, Saga 840-8502, Japan   Fax: +81(952)288548   Email: kitamura@cc.saga-u.ac.jp
,
Kensuke Muta
a   Department of Chemistry and Applied Chemistry, Graduate School of Science and Engineering, Saga University, Honjo-machi, Saga 840-8502, Japan   Fax: +81(952)288548   Email: kitamura@cc.saga-u.ac.jp
,
Mohammad Hasan Morshed
a   Department of Chemistry and Applied Chemistry, Graduate School of Science and Engineering, Saga University, Honjo-machi, Saga 840-8502, Japan   Fax: +81(952)288548   Email: kitamura@cc.saga-u.ac.jp
,
Kazutaka Muta
a   Department of Chemistry and Applied Chemistry, Graduate School of Science and Engineering, Saga University, Honjo-machi, Saga 840-8502, Japan   Fax: +81(952)288548   Email: kitamura@cc.saga-u.ac.jp
,
Keisuke Gondo
a   Department of Chemistry and Applied Chemistry, Graduate School of Science and Engineering, Saga University, Honjo-machi, Saga 840-8502, Japan   Fax: +81(952)288548   Email: kitamura@cc.saga-u.ac.jp
,
Yuji Hori
a   Department of Chemistry and Applied Chemistry, Graduate School of Science and Engineering, Saga University, Honjo-machi, Saga 840-8502, Japan   Fax: +81(952)288548   Email: kitamura@cc.saga-u.ac.jp
,
Masaya Miyazaki
b   Measurement Solution Research Center, National Institute of Advanced Industrial Science and Technology (AIST), Tosu, Saga 841-0052, Japan
› Author Affiliations
Further Information

Publication History

Received: 25 July 2013

Accepted after revision: 06 August 2013

Publication Date:
29 August 2013 (online)


Abstract

Direct fluorination of 1,3-dicarbonyl compounds including 1,3-diketones, 3-oxo esters, and 3-oxoamides was conducted using aqueous hydrofluoric acid with the aid of iodosylarenes, giving the corresponding 2-fluorinated products in good to high yields. Among the used iodosylarenes, o-iodosyltoluene was found to be the most effective, and the yield of 2-fluorinated products was improved.

Supporting Information

 
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