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36.12.9.1.4.1 Variation 1: Reductive Lithiation of Acyclic Ethers

DOI: 10.1055/sos-SD-036-00789

Morey, J. V.; Wheatley, A. E. H.Science of Synthesis, (2008361147.

Multiple examples of acyclic ether cleavage have been documented. However, in the absence of arene catalysts poor selectivity and complicating solvent effects are observed.[‌116‌] The great advantage of using a catalytic arene to encourage reductive lithiation is that the reaction conditions may be tempered considerably.[‌117‌] For example, the use of a catalytic arene has facilitated the formation of benzyl- and allyllithium species from various acyclic ethers.[‌118‌] Most recently this chemistry has been applied to benzyl methyl ethers 173, with the employment of an excess of lithium in the presence of naphthalene as a catalyst affording an alcoholate and a benzyllithium intermediate 174. Electrophilic workup and product isolation gives substituted benzyl species 175 in 3597% yield (Scheme 54).[‌119‌]

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