Synlett 2012; 23(7): 1069-1073
DOI: 10.1055/s-0031-1290758
letter
© Georg Thieme Verlag Stuttgart · New York

Carbon–Nitrogen Bond Formation between Allyl Silyl Ether and Hydrazide Promoted by Mercuric Triflate Catalyst

Authors

  • Hirofumi Yamamoto*

    a   Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Yamashiro-cho, Tokushima 770-8514, Japan, Fax: +81(88)6553051   Email: hirofumi@ph.bunri-u.ac.jp
  • Naoto Yamasaki

    a   Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Yamashiro-cho, Tokushima 770-8514, Japan, Fax: +81(88)6553051   Email: hirofumi@ph.bunri-u.ac.jp
  • Shingo Yoshidome

    a   Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Yamashiro-cho, Tokushima 770-8514, Japan, Fax: +81(88)6553051   Email: hirofumi@ph.bunri-u.ac.jp
  • Ikuo Sasaki

    a   Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Yamashiro-cho, Tokushima 770-8514, Japan, Fax: +81(88)6553051   Email: hirofumi@ph.bunri-u.ac.jp
  • Kosuke Namba

    b   Division of Chemistry, Graduate School of Science, Hokkaido University, Kita-ku, Sapporo 060-0810, Japan
  • Hiroshi Imagawa

    a   Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Yamashiro-cho, Tokushima 770-8514, Japan, Fax: +81(88)6553051   Email: hirofumi@ph.bunri-u.ac.jp
  • Mugio Nishizawa

    a   Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Yamashiro-cho, Tokushima 770-8514, Japan, Fax: +81(88)6553051   Email: hirofumi@ph.bunri-u.ac.jp
Further Information

Publication History

Received: 24 January 2012

Accepted after revision: 14 February 2012

Publication Date:
05 April 2012 (online)


Graphical Abstract

Abstract

An efficient method for carbon–nitrogen bond formation between ally silyl ethers and N,N-acyltosylhydrazine was developed under very mild conditions using 2 mol% of mercuric triflate [Hg(OTf)2] as a catalyst. This method does not require the use of any ligand system or supplementary additives and is applicable to the preparation of various N-allylhydrazides with good to excellent yields.

Supporting Information