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

Hong-Ping Zhang; Xu-Heng Yang; Peng Peng; Jin-Heng Li

doi:10.1055/s-0030-1259965

PAPER

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

Hong-Ping Zhang^a,b, Xu-Heng Yang^a, Peng Peng^a, 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

Abstract

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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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References

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Supplementary Material

Supporting Information

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

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