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Synthesis 2009(24): 4183-4189  
DOI: 10.1055/s-0029-1217037
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Iron-Catalyzed Sulfenylation of Indoles with Disulfides Promoted by a Catalytic Amount of Iodine

Xiao-Li Fang, Ri-Yuan Tang, Ping Zhong, Jin-Heng Li*
College of Chemistry and Materials Science, Wenzhou University, Wenzhou 325035, P. R. of China
Fax: +86(731)8872101; e-Mail: jhli@hunnu.edu.cn;
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Publication History

Received 24 June 2009
Publication Date:
12 October 2009 (online)

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Abstract

Selective sulfenylation of indoles with disulfides using iron(III) fluoride combined with iodine has been developed for the synthesis of sulfenylindoles. In the presence of iron(III) fluoride and iodine, a variety of disulfides underwent the reaction with indoles selectively to afford the corresponding sulfenylindoles in good to excellent yields. Moreover, reactions of indoles with 1,2-diphenyldiselane were also conducted under the same conditions, which smoothly afforded 3-selenylindoles in good yields.

Key words

iron(III) fluoride - sulfenylation - indoles - disulfides - sulfenylindoles - iodine

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