2026-04-17T10:26:30Zhttps://riubu.ubu.es/oai/requestoai:riubu.ubu.es:10259/55342021-11-02T12:05:28Zcom_10259_3593com_10259_5086com_10259_2604col_10259_3594
2020-10-29T11:25:06Z
urn:hdl:10259/5534
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
2020-08
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