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

研究成果: Article査読

8 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)692-700
ページ数9
ジャーナルSynthesis
5
DOI
出版ステータスPublished - 2004 4月 2

ASJC Scopus subject areas

  • 触媒
  • 有機化学

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