α-Lithiated Aryl Benzyl Ethers: Inhibition of [1,2]-Wittig Rearrangement and Application to the Synthesis of Benzo[b]furan Derivatives

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α-Lithiated Aryl Benzyl Ethers: Inhibition of [1,2]-Wittig Rearrangement and Application to the Synthesis of Benzo[b]furan Derivatives Velasco, Rocío Feberero, Claudia Sanz Díez, Roberto The use of t-BuLi at low temperature selectively leads to α-lithiation of benzyl phenyl ether generating a stable organolithium, which can be efficiently trapped with a variety of selected electrophiles prior to suffering the expected [1,2]-Wittig rearrangement. In the case of (o-alkynyl)phenyl benzyl ethers, the intermediate α-aryloxyorganolithium undergoes an unexpected anti intramolecular carbolithiation reaction leading to functionalized benzo[b]furan derivatives. 2016-11-21 2016-11-21 2015-09 info:eu-repo/semantics/article 1523-7060 http://hdl.handle.net/10259/4276 eng ORGANIC LETTERS. 2015, V. 17, n. 18, p. 4416–4419 http://dx.doi.org/10.1021/acs.orglett.5b01964 info:eu-repo/semantics/openAccess American Chemical Society