RT info:eu-repo/semantics/article
T1 α-Lithiobenzyloxy as a Directed Metalation Group in ortho-Lithiation Reactions
A1 Sedano Labrador, Carlos
A1 Velasco, Rocío
A1 Feberero García, Claudia
A1 Suárez Pantiga, Samuel
A1 Sanz Díez, Roberto
K1 Functionalization
K1 Ethers
K1 Rearrangement
K1 Reaction products
K1 Pharmaceuticals
K1 Química orgánica
K1 Chemistry, Organic
AB 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.
PB American Chemical Society
SN 1523-7060
YR 2020
FD 2020-08
LK http://hdl.handle.net/10259/5534
UL http://hdl.handle.net/10259/5534
LA eng
NO Ministerio de Ciencia e Innovación and FEDER (CTQ2016-75023-C2-1-P), and Junta de Castilla y León and FEDER (BU291P18)
DS Repositorio Institucional de la Universidad de Burgos
RD 22-nov-2024