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Synthesis 2011(7): 1099-1105  
DOI: 10.1055/s-0030-1258449
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

FeF3/I2-Catalyzed Synthesis of 4-Chalcogen-Substituted Arylamines by Direct Thiolation of an Arene C-H Bond

Xiao-Li Fanga, Ri-Yuan Tanga, Xing-Guo Zhang*a, Jin-Heng Li*a,b
a College of Chemistry & Materials Engineering, Wenzhou University, Wenzhou 325035, P. R. of China
b Key Laboratory of Chemical Biology & Traditional Chinese Medicine Research (Ministry of Education), Hunan Normal University, Changsha 410081, P. R. of China
Fax: +86(731)88872576; e-Mail: jhli@hunnu.edu.cn;
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Publication History

Received 30 December 2010
Publication Date:
24 February 2011 (online)

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Abstract

An efficient regioselective synthesis of 4-chalcogen-substituted­ arylamines by FeF3-catalyzed sulfenylation and selenation of arylamines has been developed. In the presence of FeF3 and I2, a variety of arylamines underwent the reaction with disulfides or diselenides to afford the corresponding 4-sulfenyl- or 4-selenenyl­arylamines in moderate to good yields.

Key words

iron - iodine - sulfenylation - selenation - arylamine - 4-chalcogen-substituted arylamine

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