2024-03-29T14:54:33Zhttps://riubu.ubu.es/oai/requestoai:riubu.ubu.es:10259/42762022-04-29T12:02:48Zcom_10259_3593com_10259_5086com_10259_2604col_10259_3594
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