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Synthesis 2011(8): 1219-1226  
DOI: 10.1055/s-0030-1259965
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

PdI2/I2-Catalyzed Thiolation-Annulation of 2-Alkynylbenzyl Azides with Disulfides: Selective Synthesis of 4-Sulfenylisoquinolines

Hong-Ping Zhanga,b, Xu-Heng Yanga, Peng Penga, Jin-Heng Li*a
a 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;
b Department of Biology and Chemistry Engineering, Shaoyang University, Shaoyang 422000, P. R. of China
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Publication History

Received 7 February 2011
Publication Date:
22 March 2011 (online)

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Abstract

A PdI2/I2-catalyzed thiolation-annulation route of alkynes with azides and disulfides for the synthesis of 4-sulfenylisoquinolines is described. This route allows numerous 2-alkynylbenzyl azides to react with disulfides or 1,2-diphenyldiselane leading to the corresponding 4-chalcogen-substituted isoquinolines in moderate to good yields.

Key words

palladium - iodine - thiolation - annulation - 2-alkynylbenzyl azides - disulfides - isoquinolines

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