Synthesis

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

T Shindo, Y Fukuyama, T Sugai

Index: Shindo, Takeyuki; Fukuyama, Yasuaki; Sugai, Takeshi Synthesis, 2004 , # 5 p. 692 - 700

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Citation Number: 3

Abstract

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. ...