Scope and limitations of lithium-ethylenediamine-THF-mediated cleavage at the α-position of aromatics: Deprotection of aryl methyl ethers and benzyl ethers under mild conditions

Takeyuki Shindo, Yasuaki Fukuyama, Takeshi Sugai

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

The scope and limitation of lithium-ethylenediamine-THF-mediated reductive bond cleavage at the α-position of aromatics were examined. Very mild conditions such as lithium metal (5 equiv) and ethylenediamine (7 equiv) in oxygen-free THF were quite effective for the demethylation of aromatic ethers even at as low as -10°C. Allyl benzyl ethers were also deprotected under these conditions with very little change of the allylic alcohol moiety. Through this study, 2,6-dimethylbenzyl (m-xylylmethyl, MXM) group was developed as an alternative of benzyl group, which is readily cleavable under the above mentioned reductive conditions.

Original languageEnglish
Pages (from-to)692-700
Number of pages9
JournalSynthesis
Issue number5
DOIs
Publication statusPublished - 2004 Apr 2

Keywords

  • Electron transfer
  • Ethers
  • Lithium
  • Phenols
  • Protective groups

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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