Direct guanylation of amino groups by cyanamide in water: Catalytic generation and activation of unsubstituted carbodiimide by scandium(iii) triflate

Kazuki Tsubokura, Takayuki Iwata, Misako Taichi, Almira Kurbangalieva, Koichi Fukase, Yoichi Nakao, Katsunori Tanaka

Research output: Contribution to journalArticlepeer-review

13 Citations (Scopus)

Abstract

Guanylation proceeded efficiently upon treatment of the various amines with cyanamide in the presence of catalytic amounts of scandium(III) triflate under mild conditions. The method did not require the guanylation reagents to be preactivated, and the reaction proceeded efficiently in water. The method, therefore, has practical utility for substrates that dissolve only in aqueous solutions, for example, peptides or pharmacologically important compounds.

Original languageEnglish
Pages (from-to)1302-1306
Number of pages5
JournalSynlett
Volume25
Issue number9
DOIs
Publication statusPublished - 2014 Jun

Keywords

  • activated carbodiimide
  • cyanamide
  • guanylation

ASJC Scopus subject areas

  • Organic Chemistry

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