2026-04-17T09:18:00Zhttps://riubu.ubu.es/oai/request

oai:riubu.ubu.es:10259/55342021-11-02T12:05:28Zcom_10259_3593com_10259_5086com_10259_2604col_10259_3594

α-Lithiobenzyloxy as a Directed Metalation Group in ortho-Lithiation Reactions Sedano Labrador, Carlos Velasco, Rocío Feberero, Claudia Suarez Pantiga, Samuel Sanz Díez, Roberto Functionalization Ethers Rearrangement Reaction products Pharmaceuticals The α-lithiobenzyloxy group, easily generated from aryl benzyl ethers by selective α-lithiation with t-BuLi at low temperature, behaves as a directed metalation group (DMG) providing a direct access to o-lithiophenyl α-lithiobenzyl ethers. This ortho-directing effect is reinforced in substrates bearing an additional methoxy group at the meta position. The generated dianions can be reacted with a selection of electrophiles including carboxylic esters and dihalosilanes or germanes, which afford interesting benzofuran, sila(germa)dihydrobenzofuran, and silachroman derivatives from simple aryl benzyl ethers. 2020-10-29T11:25:06Z 2020-10-29T11:25:06Z 2020-10-29T11:25:06Z 2020-08 info:eu-repo/semantics/article 1523-7060 http://hdl.handle.net/10259/5534 10.1021/acs.orglett.0c02199 1523-7052 eng Organic Letters. 2020, V. 22, n. 16, p. 6365–6369 https://doi.org/10.1021/acs.orglett.0c02199 info:eu-repo/grantAgreement/MICINN/CTQ2016-75023-C2-1-P info:eu-repo/grantAgreement/JCyL/BU291P18 info:eu-repo/semantics/openAccess American Chemical Society