Etherification of ferrocenyl alcohol by highly-efficient ytterbium triflate

Ran Jiang, Yechen Shen, Ying Zhang, Xiaoping Xu, Jinjun Shao, Shunjun Ji

Research output: Contribution to journalArticlepeer-review

16 Scopus citations

Abstract

Nucleophilic substitution of ferrocenyl alcohols with various aliphatic alcohols in the presence of a catalytic amount of ytterbium triflate [Yb(OTf)3] was studied. It was found the unsymmetrical ferrocenyl ethers could be easily obtained in excellent yields when the reactions were performed in primary and secondary alcohols. However, in other organic non-alcoholic solvents such as acetonitrile, the formation of symmetrical ferrocenyl ethers rather than unsymmetrical ones was observed. A convenient way for the etherification of ferrocenyl alcohols in the presence of catalytic amounts of Yb(OTf)3 was described, which afforded symmetrical ferrocenyl ethers in the non-alcoholic organic solvents and unsymmetrical ferrocenyl ethers in the alcoholic organic solvents.

Original languageEnglish
Pages (from-to)1887-1893
Number of pages7
JournalChinese Journal of Chemistry
Volume29
Issue number9
DOIs
StatePublished - Sep 2011
Externally publishedYes

Keywords

  • ferrocenyl alcohols
  • nucleophilic substitution
  • solvolysis
  • ytterbium

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