Issue 47, 2014
From the journal:

Organic & Biomolecular Chemistry

Silver(i)-catalyzed annulation for the regioselective synthesis of N-imino-γ-carbolinium ylides from hydrazones of indole-3-carbonyl derivatives and propargylic alcohols†

Yu Zhu,a   Xin-Rui Shen,a   Hai-Tao Tang,a   Min Lina  and  Zhuang-Ping Zhan*a  

* Corresponding authors

a Department of Chemistry and Key Laboratory for Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian, People's Republic of China
E-mail: zpzhan@xmu.edu.cn

Abstract

A regioselective efficient synthetic approach to N-imino-γ-carbolinium ylides via AgOTf-catalyzed iminoannulation has been developed. This transformation proceeds via a silver(I) triflate-catalyzed consecutive Friedel–Crafts reaction/N–C bond formation sequence between the readily available indole derivatives and propargylic alcohols.

Graphical abstract: Silver(i)-catalyzed annulation for the regioselective synthesis of N-imino-γ-carbolinium ylides from hydrazones of indole-3-carbonyl derivatives and propargylic alcohols

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Article information

DOI
https://doi.org/10.1039/C4OB02020K
Article type
Communication
Submitted
22 Sep 2014
Accepted
15 Oct 2014
First published
16 Oct 2014

Org. Biomol. Chem., 2014,12, 9514-9518

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Silver(I)-catalyzed annulation for the regioselective synthesis of N-imino-γ-carbolinium ylides from hydrazones of indole-3-carbonyl derivatives and propargylic alcohols

Y. Zhu, X. Shen, H. Tang, M. Lin and Z. Zhan, Org. Biomol. Chem., 2014, 12, 9514 DOI: 10.1039/C4OB02020K

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